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Highly diastereoselective nitroaldol reactions with chiral derivatives of glyoxylic acid |
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| Authors: | Iwona KudybaJerzy Raczko Janusz Jurczak |
| Institution: | a Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland b ZD CHEMIPAN, Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland c Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland |
| Abstract: | N-Glyoxyloyl-(2R)-bornane-10,2-sultam (1a) and (1R)-8-phenylmenthyl glyoxylate (1b) react stereoselectively with simple nitroalkanes giving diastereomeric nitroalcohols with high asymmetric induction. The glyoximide 1a is proved to be a highly efficient chiral inducer, superior to glyoxylate 1b. In all cases, the absolute configuration (2S) and relative configuration, syn for the major diastereoisomers, were confirmed. |
| Keywords: | nitroalcohols nitroaldol reaction asymmetric induction chiral auxiliary |
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