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1
Supporting Information
Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates
John Kallikat Augustine,* a Agnes Bombrun,b Srinivasa Venkatachaliah,a Anandh Jothia
aSyngene International Ltd., Biocon Park, Plot Nos. 2 & 3, Bommasandra IV Phase, Jigani Link
Road, Bangalore - 560 099, India.
bCovance Central Laboratory Services, 7 Rue Moise-Marcinhes, 1217 Meyrin, Geneva, Switzerland.
Table of contents
Table of contents.………………………………………………….... 1 1H NMR, 13C NMR, HPLC and IR reports for 1aE…….………… 2-5 1H NMR, 13C NMR, HPLC and IR reports for 1a-1q…….………… 6-73 1H NMR, 13C NMR, HPLC and IR reports for 2a-2j……….………. 74-113 1H NMR, 13C NMR, HPLC and IR reports for 3a-3i……….………. 114-149 1H NMR, 13C NMR, HPLC and IR reports for 4a-4j……….………. 150-189 1H NMR, 13C NMR reports for 5 …………………….……….……. 190-191
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
2
(E)-isomer (1aE): 1H NMR (400 MHz) in DMSO-d6
Br
BrCOOMe
H
1aE
delta 7.54 ppm
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
3
13C NMR (100 MHz) in CDCl3 (1aE)
Br
BrCOOMe
1aE
(E)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
4
IR data (1aE)
Br
BrCOOMe
1aE
(E)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
5
HPLC data (1aE)
Br
BrCOOMe
1aE
(E)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
6
(Z)-isomer (1a): 1H NMR (400 MHz) in DMSO-d6
Br
COOMe
Br
H
1a
delta 8.25 ppm
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
7
13C NMR (100 MHz) in CDCl3 (1a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
8
IR spectrum (1a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
9
HPLC data (1a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
10
1H NMR (400 MHz) in CDCl3 (1b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
11
13C NMR (100 MHz) in CDCl3 (1b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
12
IR spectrum (1b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
13
HPLC data (1b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
14
1H NMR (400 MHz) in CDCl3 (1c)
Br
O
O(Z)
(1c)N
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
15
13C NMR (100 MHz) in CDCl3 (1c)
Br
O
O(Z)
(1c)N
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
16
IR spectrum (1c)
Br
O
O(Z)
(1c)N
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
17
HPLC data (1c)
Br
O
O(Z)
(1c)N
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
18
1H NMR (400 MHz) in DMSO-d6 (1d)
Br
O
O
O
O
(Z)
(1d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
19
13C NMR (100 MHz) in CDCl3 (1d)
Br
O
O
O
O
(Z)
(1d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
20
IR spectrum (1d)
Br
O
O
O
O
(Z)
(1d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
21
HPLC data (1d)
Br
O
O
O
O
(Z)
(1d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
22
1H NMR (400 MHz) in CDCl3 (1e)
Br
O
O
Br
Cl(Z)
(1e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
23
13C NMR (100 MHz) in CDCl3 (1e)
Br
O
O
Br
Cl(Z)
(1e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
24
IR spectrum (1e)
Br
O
O
Br
Cl(Z)
(1e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
25
HPLC data (1e)
Br
O
O
Br
Cl(Z)
(1e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
26
1H NMR (400 MHz) in CDCl3 (1f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
27
13C NMR (100 MHz) in CDCl3 (1f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
28
IR spectrum (1f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
29
HPLC data (1f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
30
1H NMR (400 MHz) in CDCl3 (1g)
O
O
BrNC
(Z)
(1g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
31
13C NMR (100 MHz) in CDCl3 (1g)
O
O
BrNC
(Z)
(1g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
32
IR spectrum (1g)
O
O
BrNC
(Z)
(1g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
33
HPLC data (1g)
O
O
BrNC
(Z)
(1g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
34
1H NMR (400 MHz) in CDCl3 (1h)
O
O
Br
(Z)
(1h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
35
13C NMR (100 MHz) in CDCl3 (1h)
O
O
Br
(Z)
(1h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
36
IR spectrum (1h)
O
O
Br
(Z)
(1h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
37
HPLC data (1h)
O
O
Br
(Z)
(1h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
38
1H NMR (400 MHz) in DMSO-d6 (1i)
( Z )
(1i)N
Br
COOMe
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
39
13C NMR (100 MHz) in DMSO-d6 (1i)
( Z )
(1i)N
Br
COOMe
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
40
IR spectrum (1i)
( Z )
(1i)N
Br
COOMe
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
41
HPLC data (1i)
( Z )
(1i)N
Br
COOMe
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
42
1H NMR (400 MHz) in CDCl3 (1j)
NBr
O
O
F
F
( Z)
(1j)
F
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
43
13C NMR (100 MHz) in CDCl3 (1j)
NBr
O
O
F
F
( Z)
(1j)
F
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
44
IR spectrum (1j)
NBr
O
O
F
F
( Z)
(1j)
F
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
45
HPLC data (1j)
NBr
O
O
F
F
( Z)
(1j)
F
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
46
1H NMR (400 MHz) in CDCl3 (1k)
(1k)Br
COOMeSBr
(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
47
13C NMR (100 MHz) in CDCl3 (1k)
(1k)Br
COOMeSBr
(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
48
IR spectrum (1k)
(1k)Br
COOMeSBr
(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
49
HPLC data (1k)
(1k)Br
COOMeSBr
(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
50
1H NMR (400 MHz) in CDCl3 (1l)
(Z)
(1l)Br
COOMeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
51
13C NMR (100 MHz) in CDCl3 (1l)
(Z)
(1l)Br
COOMeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
52
IR spectrum (1l)
(Z)
(1l)Br
COOMeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
53
HPLC data (1l)
(Z)
(1l)Br
COOMeO
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
54
1H NMR (400 MHz) in CDCl3 (1m)
( Z )
Br
O
O
(1m)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
55
13C NMR (100 MHz) in CDCl3 (1m)
( Z )
Br
O
O
(1m)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
56
IR spectrum (1m)
( Z )
Br
O
O
(1m)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
57
HPLC data (1m)
( Z )
Br
O
O
(1m)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
58
1H NMR (400 MHz) in CDCl3 (1n)
( Z )
Br
O
O
(1n)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
59
13C NMR (100 MHz) in CDCl3 (1n)
( Z )
Br
O
O
(1n)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
60
IR spectrum (1n)
( Z )
Br
O
O
(1n)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
61
HPLC data (1n)
( Z )
Br
O
O
(1n)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
62
1H NMR (400 MHz) in CDCl3 (1o)
( Z )
Br
O
O
(1o)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
63
13C NMR (100 MHz) in CDCl3 (1o)
( Z )
Br
O
O
(1o)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
64
IR spectrum (1o)
( Z )
Br
O
O
(1o)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
65
HPLC data (1o)
( Z )
Br
O
O
(1o)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
66
1H NMR (400 MHz) in CDCl3 (1p)
( Z )
Br
O
OOMe
(1p)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
67
13C NMR (100 MHz) in CDCl3 (1p)
( Z )
Br
O
OOMe
(1p)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
68
IR spectrum (1p)
( Z )
Br
O
OOMe
(1p)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
69
HPLC data (1p)
( Z )
Br
O
OOMe
(1p)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
70
1H NMR (400 MHz) in DMSO-d6 (1q)
Br
OH
O
O(Z)
(1q)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
71
13C NMR (100 MHz) in DMSO-d6 (1q)
Br
OH
O
O(Z)
(1q)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
72
IR spectrum (1q)
Br
OH
O
O(Z)
(1q)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
73
HPLC data (1q)
Br
OH
O
O(Z)
(1q)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
74
1H NMR (400 MHz) in DMSO-d6 (2a)
ClO
O(Z)
(2a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
75
13C NMR (100 MHz) in DMSO-d6 (2a)
ClO
O(Z)
(2a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
76
IR spectrum (2a)
ClO
O(Z)
(2a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
77
HPLC data (2a)
ClO
O(Z)
(2a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
78
1H NMR (400 MHz) in DMSO-d6 (2b)
ClO
O(Z)
Br(2b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
79
13C NMR (100 MHz) in DMSO-d6 (2b)
ClO
O(Z)
Br(2b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
80
IR spectrum (2b)
ClO
O(Z)
Br(2b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
81
HPLC data (2b)
ClO
O(Z)
Br(2b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
82
1H NMR (400 MHz) in DMSO-d6 (2c)
O
O
O
Cl
(Z)
(2c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
83
13C NMR (100 MHz) in DMSO-d6 (2c)
O
O
O
Cl
(Z)
(2c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
84
IR spectrum (2c)
O
O
O
Cl
(Z)
(2c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
85
HPLC data (2c)
O
O
O
Cl
(Z)
(2c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
86
1H NMR (400 MHz) in CDCl3 (2d)
NCCl
O
O(Z)
(2d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
87
1H NMR (100 MHz) in CDCl3 (2d)
NCCl
O
O(Z)
(2d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
88
IR spectrum (2d)
NCCl
O
O(Z)
(2d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
89
HPLC data (2d)
NCCl
O
O(Z)
(2d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
90
1H NMR (400 MHz) in CDCl3 (2e)
O
O
Cl
F
FF
(Z)NO2
(2e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
91
13C NMR (100 MHz) in CDCl3 (2e)
O
O
Cl
F
FF
(Z)NO2
(2e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
92
IR spectrum (2e)
O
O
Cl
F
FF
(Z)NO2
(2e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
93
HPLC data (2e)
O
O
Cl
F
FF
(Z)NO2
(2e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
94
1H NMR (400 MHz) in DMSO-d6 (2f)
OO
O
Cl
(Z)
(2f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
95
13C NMR (100 MHz) in DMSO-d6 (2f)
OO
O
Cl
(Z)
(2f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
96
IR spectrum (2f)
OO
O
Cl
(Z)
(2f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
97
HPLC data (2f)
OO
O
Cl
(Z)
(2f)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
98
1H NMR (400 MHz) in DMSO-d6 (2g)
NO
O
O
Cl
(Z)
(2g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
99
13C NMR (100 MHz) in DMSO-d6 (2g)
NO
O
O
Cl
(Z)
(2g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
100
IR spectrum (2g)
NO
O
O
Cl
(Z)
(2g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
101
HPLC data (2g)
NO
O
O
Cl
(Z)
(2g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
102
1H NMR (400 MHz) in CDCl3 (2h)
O
O
ClO2N
(Z)
(2h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
103
13C NMR (100 MHz) in CDCl3 (2h)
O
O
ClO2N
(Z)
(2h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
104
IR spectrum (2h)
O
O
ClO2N
(Z)
(2h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
105
HPLC data (2h)
O
O
ClO2N
(Z)
(2h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
106
1H NMR (400 MHz) in CDCl3 (2i)
O
O
Cl
(Z)
(2i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
107
13C NMR (100 MHz) in CDCl3 (2i)
O
O
Cl
(Z)
(2i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
108
IR spectrum (2i)
O
O
Cl
(Z)
(2i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
109
HPLC data (2i)
O
O
Cl
(Z)
(2i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
110
1H NMR (400 MHz) in CDCl3 (2j)
O
O
Cl
(Z)
(2j)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
111
13C NMR (100 MHz) in CDCl3 (2j)
O
O
Cl
(Z)
(2j)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
112
IR spectrum (2j)
O
O
Cl
(Z)
(2j)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
113
HPLC data (2j)
O
O
Cl
(Z)
(2j)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
114
1H NMR (400 MHz) in CDCl3 (3a)
F
O
O(Z)
(3a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
115
13C NMR (100 MHz) in CDCl3 (3a)
F
O
O(Z)
(3a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
116
IR spectrum (3a)
F
O
O(Z)
(3a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
117
HPLC data (3a)
F
O
O(Z)
(3a)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
118
1H NMR (400 MHz) in CDCl3 (3b)
BrF
O
O(Z)
(3b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
119
13C NMR (100 MHz) in CDCl3 (3b)
BrF
O
O(Z)
(3b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
120
IR spectrum (3b)
BrF
O
O(Z)
(3b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
121
HPLC data (3b)
BrF
O
O(Z)
(3b)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
122
1H NMR (100 MHz) in CDCl3 (3c)
OF
O
O(Z)
(3c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
123
13C NMR (100 MHz) in CDCl3 (3c)
OF
O
O(Z)
(3c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
124
IR spectrum (3c)
OF
O
O(Z)
(3c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
125
HPLC data (3c)
OF
O
O(Z)
(3c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
126
1H NMR (400 MHz) in CDCl3 (3d)
NCF
O
O(Z)
(3d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
127
13C NMR (100 MHz) in CDCl3 (3d)
NCF
O
O(Z)
(3d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
128
IR spectrum (3d)
NCF
O
O(Z)
(3d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
129
HPLC data (3d)
NCF
O
O(Z)
(3d)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
130
1H NMR (400 MHz) in CDCl3 (3e)
NO2
F
F
FF
O
O(Z)
(3e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
131
13C NMR (100 MHz) in CDCl3 (3e)
NO2
F
F
FF
O
O(Z)
(3e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
132
IR spectrum (3e)
NO2
F
F
FF
O
O(Z)
(3e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
133
HPLC data (3e)
NO2
F
F
FF
O
O(Z)
(3e)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
134
1H NMR (400 MHz) in CDCl3 (3f)
O
F
O
O
(Z)
(3f )
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
135
13C NMR (100 MHz) in CDCl3 (3f)
O
F
O
O
(Z)
(3f )
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
136
IR spectrum (3f)
O
F
O
O
(Z)
(3f )
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
137
HPLC spectrum (3f)
O
F
O
O
(Z)
(3f )
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
138
1H NMR (400 MHz) in CDCl3 (3g)
NOF
O
O(Z)
(3g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
139
13C NMR (100 MHz) in CDCl3 (3g)
NOF
O
O(Z)
(3g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
140
IR spectrum (3g)
NOF
O
O(Z)
(3g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
141
HPLC data (3g)
NOF
O
O(Z)
(3g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
142
1H NMR (400 MHz) in CDCl3 (3h)
FO
O
O2N
(Z)
(3h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
143
13C NMR (100 MHz) in CDCl3 (3h)
F
O
O
O2N
(Z)
(3h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
144
IR spectrum (3h)
FO
O
O2N
(Z)
(3h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
145
HPLC data (3h)
F
O
O
O2N
(Z)
(3h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
146
1H NMR (400 MHz) in CDCl3 (3i)
F
O
O(Z)
(3i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
147
13C NMR (100 MHz) in CDCl3 (3i)
F
O
O(Z)
(3i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
148
IR spectrum (3i)
F
O
O(Z)
(3i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
149
HPLC data (3i)
F
O
O(Z)
(3i)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
150
1H NMR (400 MHz) in CDCl3 (4a)
I
O
O
(Z)
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
151
13c NMR (100 MHz) in CDCl3 (4a)
I
O
O
(Z)
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
152
IR spectrum (4a)
I
O
O
(Z)
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
153
HPLC spectrum (4a)
I
O
O
(Z)
4a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
154
1H NMR (400 MHz) in CDCl3 (4b)
IO
O(Z)
Br 4b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
155
13c NMR (100 MHz) in CDCl3 (4b)
IO
O(Z)
Br 4b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
156
IR spectrum (4b)
IO
O(Z)
Br 4b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
157
HPLC data (4b)
IO
O(Z)
Br 4b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
158
1H NMR (400 MHz) in CDCl3 (4c)
IO
O(Z)
O 4c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
159
13C NMR (100 MHz) in CDCl3 (4c)
IO
O(Z)
O 4c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
160
IR spectrum (4c)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
161
HPLC data (4c)
IO
O(Z)
O 4c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
162
1H NMR (400 MHz) in CDCl3 (4d)
IO
O(Z)
CN 4d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
163
13C NMR (100 MHz) in CDCl3 (4d)
IO
O(Z)
CN 4d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
164
IR spectrum (4d)
IO
O(Z)
CN 4d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
165
HPLC data (4d)
IO
O(Z)
CN 4d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
166
1H NMR (400 MHz) in CDCl3 (4e)
4eI
O
O(Z)
FF
F
NO2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
167
13C NMR (100 MHz) in CDCl3 (4e)
4eI
O
O(Z)
FF
F
NO2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
168
IR spectrum (4e)
4eI
O
O(Z)
FF
F
NO2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
169
HPLC data (4e)
4eI
O
O(Z)
FF
F
NO2
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
170
1H NMR (400 MHz) in CDCl3 (4f)
4f
OI O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
171
13C NMR (100 MHz) in CDCl3 (4f)
4f
OI O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
172
IR spectrum (4f)
4f
OI O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
173
HPLC data (4f)
4f
OI O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
174
1H NMR (400 MHz) in CDCl3 (4g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
175
13C NMR (100 MHz) in CDCl3 (4g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
176
IR spectrum (4g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
177
HPLC data (4g)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
178
1H NMR (400 MHz) in DMSO-d6 (4h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
179
13C NMR (100 MHz) in DMSO-d6 (4h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
180
IR spectrum (4h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
181
HPLC data (4h)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
182
1H NMR (400 MHz) in CDCl3 (4i)
4iI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
183
13C NMR (100 MHz) in CDCl3 (4i)
4iI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
184
IR spectrum (4i)
4iI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
185
HPLC data (4i)
4iI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
186
1H NMR (400 MHz) in CDCl3 (4j)
4jI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
187
13C NMR (100 MHz) in CDCl3 (4j)
4jI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
188
IR spectrum (4j)
4jI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
189
HPLC data (4j)
4jI
O
O(Z)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
190
1H NMR (400 MHz) in CDCl3 (5)
O
OO
O
(5)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013
191
13C NMR (100 MHz) in CDCl3 (5)
**************************
O
OO
O
(5)
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013