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  • Organocatalytic asymmetric direct vinylogous Michael addition of ,- unsaturated -butyrolactam to nitroolefins

    Abhijnan Ray Choudhury and Santanu Mukherjee*

    Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, INDIA

    sm@orgchem.iisc.ernet.in

    SUPPORTING INFORMATION: PART B

    Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is The Royal Society of Chemistry 2012

  • Ray Choudhury & Mukherjee, SI-Part-B, Page S-2

    10 9 8 7 6 5 4 3 2 1 0 ppm

    4.00

    14.

    006

    6.09

    06.

    095

    6.09

    8

    7.10

    87.

    112

    8.17

    4

    2.11

    0

    0.92

    9

    0.94

    9

    1.00

    0

    200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

    49.0

    89

    76.8

    4577

    .164

    77.4

    82

    127.

    592

    146.

    099

    175.

    679

    NH

    O

    NH

    O

    Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is The Royal Society of Chemistry 2012

  • Ray Choudhury & Mukherjee, SI-Part-B, Page S-3

    10 9 8 7 6 5 4 3 2 1 0 ppm

    1.53

    0

    4.32

    7

    6.12

    46.

    128

    6.13

    56.

    140

    7.16

    47.

    169

    7.17

    57.

    180

    9.32

    5

    2.04

    9

    0.96

    4

    1.00

    0

    200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

    28.0

    04

    51.5

    72

    76.6

    8677

    .004

    77.3

    2282

    .894

    127.

    827

    145.

    114

    149.

    473

    169.

    094

    \

    N O

    Boc1

    N O

    Boc1

    Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is The Royal Society of Chemistry 2012

  • Ray Choudhury & Mukherjee, SI-Part-B, Page S-4

    10 9 8 7 6 5 4 3 2 1 0 ppm

    0.87

    40.

    887

    1.27

    01.

    289

    1.30

    61.

    351

    1.37

    61.

    693

    2.03

    72.

    244

    2.27

    12.

    300

    2.34

    12.

    669

    2.83

    82.

    865

    2.89

    23.

    050

    3.39

    63.

    414

    3.79

    73.

    815

    4.98

    15.

    006

    5.04

    95.

    370

    6.01

    36.

    058

    6.07

    8

    7.03

    87.

    301

    7.42

    57.

    569

    7.58

    07.

    886

    7.90

    9

    8.61

    08.

    620

    1.19

    6

    2.12

    3

    1.05

    1

    0.90

    0

    1.78

    6

    0.83

    30.

    998

    0.87

    7

    0.81

    3

    1.78

    8

    1.89

    2

    2.03

    10.

    885

    1.12

    51.

    026

    0.91

    5

    1.00

    0

    N

    HN

    OH

    OH

    III

    Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is The Royal Society of Chemistry 2012

  • Ray Choudhury & Mukherjee, SI-Part-B, Page S-5

    10 9 8 7 6 5 4 3 2 1 0 ppm

    1.00

    01.

    017

    1.12

    41.

    248

    1.48

    01.

    504

    1.52

    41.

    754

    2.00

    72.

    031

    2.03

    62.

    043

    2.06

    32.

    079

    2.09

    52.

    220

    2.24

    12.

    754

    2.76

    42.

    785

    2.87

    52.

    900

    2.90

    82.

    933

    3.04

    63.

    056

    3.34

    73.

    366

    3.71

    03.

    726

    5.01

    95.

    027

    5.05

    75.

    608

    5.61

    75.

    998

    6.02

    37.

    137

    7.14

    37.

    265

    7.27

    17.

    277

    7.29

    47.

    300

    7.49

    97.

    511

    7.91

    47.

    937

    8.58

    08.

    591

    5.86

    21.

    016

    1.27

    12.

    214

    1.02

    42.

    139

    0.94

    8

    1.17

    82.

    053

    1.03

    21.

    043

    1.93

    2

    1.91

    3

    0.91

    4

    0.94

    2

    1.06

    90.

    895

    1.00

    7

    1.01

    1

    1.00

    0

    200 180 160 140 120 100 80 60 40 20 0 ppm

    19.2

    2821

    .063

    26.2

    2228

    .171

    39.8

    86

    49.5

    4150

    .088

    59.6

    2571

    .667

    74.5

    8676

    .682

    77.0

    0077

    .318

    101.

    776

    114.

    600

    118.

    412

    121.

    850

    121.

    855

    126.

    545

    131.

    335

    140.

    389

    143.

    944

    147.

    311

    147.

    408

    157.

    284

    N

    HN

    OH

    OIV

    N

    HN

    OH

    OIV

    Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is The Royal Society of Chemistry 2012

  • Ray Choudhury & Mukherjee, SI-Part-B, Page S-6

    10 9 8 7 6 5 4 3 2 1 0 ppm

    0.82

    20.

    840

    0.85

    80.

    963

    0.97

    60.

    996

    1.01

    81.

    029

    1.34

    01.

    359

    1.37

    71.

    408

    1.42

    51.

    642

    1.93

    61.

    961

    1.99

    12.

    664

    2.67

    42.

    696

    2.71

    72.

    787

    2.81

    42.

    838

    2.84

    62.

    871

    2.92

    82.

    943

    2.94

    82.

    964

    3.09

    23.

    111

    3.12

    33.

    143

    3.76

    25.

    264

    5.57

    85.

    585

    7.12

    17.

    187

    7.19

    27.

    210

    7.21

    57.

    260

    7.47

    27.

    483

    7.84

    27.

    864

    8.45

    98.

    470

    3.23

    81.

    073

    4.05

    71.

    055

    0.99

    8

    1.09

    72.

    024

    0.97

    81.

    031

    3.18

    1

    1.25

    2

    1.02

    40.

    977

    0.98

    1

    1.00

    2

    1.00

    0

    N

    HN

    OH

    OMeV

    Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is The Royal Society of Chemistry 2012

  • Ray Choudhury & Mukherjee, SI-Part-B, Page S-7

    10 9 8 7 6 5 4 3 2 1 0 ppm

    0.92

    60.

    942

    1.24

    81.

    515

    1.54

    81.

    562

    1.57

    81.

    672

    1.86

    11.

    940

    1.96

    21.

    995

    2.25

    52.

    275

    2.29

    52.

    315

    2.66

    12.

    704

    2.72

    62.

    896

    2.91

    73.

    333

    3.95

    95.

    093

    5.12

    45.

    136

    5.14

    95.

    985

    6.00

    46.

    011

    6.02

    96.

    046

    6.05

    46.

    072

    7.26

    37.

    339

    7.39

    17.

    397

    7.41

    47.

    420

    7.45

    48.

    037

    8.06

    08.

    789

    8.80

    0

    1.09

    0

    2.48

    91.

    134

    1.09

    81.

    172

    1.14

    8

    4.83

    21.

    975

    0.94

    3

    3.31

    5

    2.01

    1

    1.07

    0

    3.12

    0

    1.07

    3

    1.00

    0

    N

    HN

    OMs

    OMe

    Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is The Royal Society of Chemistry 2012

  • Ray Choudhury & Mukherjee, SI-Part-B, Page S-8

    10 9 8 7 6 5 4 3 2 1 0 ppm

    1.09

    01.

    104

    1.12

    41.

    145

    1.15

    71.

    352

    1.37

    51.

    405

    1.71

    01.

    729

    1.74

    71.

    809

    2.47

    42.

    489

    3.18

    53.

    206

    3.22

    83.

    274

    3.30

    13.

    321

    3.37

    13.

    394

    3.41

    53.

    476

    3.93

    35.

    168

    5.19

    35.

    229

    5.29

    05.

    348

    5.37

    25.

    807

    5.82

    15.

    833

    5.84

    95.

    865

    5.87

    65.

    891

    7.26

    07.

    348

    7.35

    37.

    371

    7.37

    67.

    487

    7.49

    77.

    572

    7.99

    88.

    021

    8.72

    98.

    739

    1.25

    71.

    979

    3.12

    1

    0.87

    4

    4.78

    8

    3.05

    5

    1.82

    71.

    121

    0.86

    2

    1.09

    60.

    939

    0.92

    1

    1.02

    8

    1.00

    0

    N

    HN

    OH

    OMe

    VI

    Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is The Royal Society of Chemistry 2012

  • Ray Choudhury & Mukherjee, SI-Part-B, Page S-9

    10 9 8 7 6 5 4 3 2 1 0 ppm

    1.26

    71.

    283

    1.29

    91.

    623

    1.64

    41.

    656

    1.67

    51.

    693

    1.71

    01.

    730

    1.80

    21.

    819

    1.83

    41.

    851

    2.21

    32.

    225

    2.77

    82.

    812

    2.97

    02.

    992

    3.02

    23.

    043

    3.09

    03.

    111

    3.14

    33.

    725

    3.74

    13.

    758

    5.93

    2

    7.26

    47.

    281

    7.28

    87.

    304

    7.31

    07.

    590

    7.60

    17.

    656

    7.66

    17.

    937

    7.96

    08.

    683

    8.69

    4

    9.39

    1

    3.00

    01.

    024

    1.09

    23.

    197

    1.26

    81.

    068

    0.96

    81.

    195

    0.98

    5

    1.88

    5

    0.97

    4

    1.25

    21.

    074

    0.92

    71.

    404

    1.16

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