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The significantly higher enantiomeric ratios obtained with compounds 3 / 5a and 3 / 5f and in large-scale reactions might suggest an enrichment of the enantiomeric ratio by partial crystallization of these products; however, several experiments in two different laboratories and the use of polar solvents to avoid unintentional crystallization by manipulation of the samples ruled out this possibility; nonlinear effects and other experimental issues could affect the enantioselectivity.
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The yield of nitrone 5a was increased to 80% by shortening the reaction time to 5-10min and using freshly activated Zn.
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CCDC-777231 (rac-5 a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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CCDC-777232 ((2R,3S,4R)- 6 e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via. The data set was collected with a Nonius KappaCCD diffractometer; programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol, 1997, 276, 307-326), absorption correction Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. 2003, A59, 228-234), structure solution SHELXS-97 (G.M. Sheldrick, Acta Crystallogr. Sect. A. 1990, 46, 467-473), structure refinement SHELXL-97 (G.M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122), graphics SCHAKAL (E. Keller, Univ. Freiburg, 1997).
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CCDC-777232 ((2R,3S,4R)- 6 e) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via. The data set was collected with a Nonius KappaCCD diffractometer; programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol, 1997, 276, 307-326), absorption correction Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. 2003, A59, 228-234), structure solution SHELXS-97 (G.M. Sheldrick, Acta Crystallogr. Sect. A. 1990, 46, 467-473), structure refinement SHELXL-97 (G.M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122), graphics SCHAKAL (E. Keller, Univ. Freiburg, 1997).
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