construction of dispirocyclohexanes via amine-catalyzed [2 + 2 + … · construction of...
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Electronic Supplementary Information
Construction of Dispirocyclohexanes via Amine-Catalyzed [2 + 2 + 2]
Annulations of Morita-Baylis-Hillman Acetates with Exocyclic Alkenes
Rongshun Chen,a Silong Xu,b* Xia Fan,a Hanyuan Li,a Yuhai Tang,b and Zhengjie Hea*
a The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Collaborative Innovation Center of
Chemical Science and Engineering (Tianjin), 94 Weijin Road, Tianjin 300071, P. R. China.
Fax: +86 22 23501520; e-mail: [email protected] b Department of Chemistry, School of Science, Xi’an Jiaotong University, Xi’an 710049, P. R. China.
Fax: +86 29 82655399; e-mail: [email protected]
Table of Contents
I. ORTEP Representation of 3r and 5f ........................................................................ S2
II. NMR Spectra for 3 and 5 ....................................................................................... S4
III. NOESY Spectra for Compound 5a ..................................................................... S93
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2014
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I. ORTEP Representation of 3r and 5f
Table S1. Crystal data and structure refinement for 3r
Identification code 3r
Empirical formula C43H32F6O6
Formula weight 758.69
Temperature 173(2) K
Wavelength 0.71073 Å,
Crystal system, space group Monoclinic, P2(1)/c
Unit cell dimensions a = 12.174(2) Å =90°
b = 21.206(4) Å = 92.65(3) °
c = 14.570(3) Å, = 90°.
Volume 3757.4(13) Å3
Z, Calculated density 4, 1.379 Mg/m3
Absorption coefficient 0.145 mm-1
F(000) 16100
Crystal size 0.20 x 0.18 x 0.12 mm3
Theta range for data collection 1.70 to 27.94°.
Limiting indices -16<=h<=14, -27<=k<=27, -19<=l<=19
Reflections collected / unique 37451 / 8963 [R(int) = 0.0769]
Completeness to the θ = 25.02° 99.5 %
Absorption correction Semi-empirical from equivalents
Max. and min. transmission 0.9828 and 0.9716
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 8963 / 78 / 551
Goodness-of-fit on F2 0.981
Final R indices[I>2σ(I)] R1 = 0.0613, wR2 = 0.1365
R indices (all data) R1 = 0.1068, wR2 = 0.1590
Largest diff. peak and hole 0.296 and -0.324 e. Å-3
Figure S1. ORTEP Drawing for 3r
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Table S2. Crystal data and structure refinement for 5f
Identification code 5f
Empirical formula C37H41N2O10
Formula weight 673.72
Temperature 293(2) K
Wavelength 0.71073 Å,
Crystal system, space group Triclinic, P-1
Unit cell dimensions a = 10.530(2) Å = 65.69(3)°
b = 13.602(3) Å = 80.28(3) °
c = 13.650(3) Å, = 81.84(3)°.
Volume 1750.5(6) Å3
Z, Calculated density 2, 1.278 Mg/m3
Absorption coefficient 0.093 mm-1
F(000) 714
Crystal size 0.20 x 0.18 x 0.12 mm3
Theta range for data collection 1.81 to 29.07°.
Limiting indices -14<=h<=14, -18<=k<=14, -18<=l<=17
Reflections collected / unique 18820 / 8967 [R(int) = 0.0425]
Completeness to the θ = 25.02° 95.6 %
Absorption correction Semi-empirical from equivalents
Max. and min. transmission 0.9889 and 0.9816
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 8967 / 84 / 472
Goodness-of-fit on F2 0.998
Final R indices[I>2σ(I)] R1 = 0.0535, wR2 = 0.1128
R indices (all data) R1 = 0.1238, wR2 = 0.1361
Largest diff. peak and hole 0.366 and -0.361 e. Å-3
Figure S2. ORTEP Drawing for 5f
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II. NMR Spectra for 3 and 5
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III. NOESY Spectra for Compound 5a
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