Highly diastereoselective Henry reaction of nitro compounds with chiral derivatives of glyoxylic acid

N-Glyoxyloyl-(2 R)-bornane-10,2-sultam and (1 R)-8-phenylmenthyl glyoxylate react stereoselectively with simple nitro compounds giving diastereoisomeric nitroalcohols with high asymmetric induction. N-Glyoxyloyl-(2 R)-bornane-10,2-sultam 1a is shown to be a highly efficient chiral inducer, superior...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 22; pp. 4807 - 4820
Main Authors Kudyba, Iwona, Raczko, Jerzy, Urbańczyk-Lipkowska, Zofia, Jurczak, Janusz
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 24.05.2004
Elsevier
Subjects
Asymmetric induction
Chemistry
Chemistry, Organic
Chiral auxiliary
Nitro compounds
Nitroalcohols
Nitroaldol reaction
Physical Sciences
Science & Technology
Nitro compounds
Nitroalcohols
Chiral auxiliary
Nitroaldol reaction
Asymmetric induction
nitroalcohols
asymmetric induction
ROUTE
chiral auxiliary
AMINO
nitroaldol reaction
nitro compounds
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Summary:N-Glyoxyloyl-(2 R)-bornane-10,2-sultam and (1 R)-8-phenylmenthyl glyoxylate react stereoselectively with simple nitro compounds giving diastereoisomeric nitroalcohols with high asymmetric induction. N-Glyoxyloyl-(2 R)-bornane-10,2-sultam 1a is shown to be a highly efficient chiral inducer, superior to (1 R)-8-phenylmenthyl glyoxylate 1b . In all cases, the absolute (2 S) configuration at the center bearing the hydroxy group and the relative syn configuration for the major diastereoisomers were determined. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.04.005