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Highly diastereoselective Henry reaction of nitro compounds with chiral derivatives of glyoxylic acid |
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| Authors: | Iwona Kudyba Zofia Urbańczyk-Lipkowska |
| 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 and (1R)-8-phenylmenthyl glyoxylate react stereoselectively with simple nitro compounds giving diastereoisomeric nitroalcohols with high asymmetric induction. N-Glyoxyloyl-(2R)-bornane-10,2-sultam 1a is shown to be a highly efficient chiral inducer, superior to (1R)-8-phenylmenthyl glyoxylate 1b. In all cases, the absolute (2S) configuration at the center bearing the hydroxy group and the relative syn configuration for the major diastereoisomers were determined. |
| Keywords: | Nitroalcohols Nitroaldol reaction Asymmetric induction Nitro compounds Chiral auxiliary |
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