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Asymmetric Reaction of Simple Nitro Compounds with Chiral 1,3‐Oxazolidin‐2‐ones
Author(s) -
Kudyba Iwona,
Raczko Jerzy,
Jurczak Janusz
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490156
Subject(s) - chemistry , nitro , diastereomer , asymmetric induction , acetaldehyde , aldol reaction , stereochemistry , derivative (finance) , alcohol , medicinal chemistry , chiral auxiliary , absolute configuration , catalysis , enantioselective synthesis , organic chemistry , ethanol , alkyl , financial economics , economics
The chiral oxazolidinone 1 (=[(3a S ,6 R ,7a R )‐tetrahydro‐8,8‐dimethyl‐2‐oxo‐4 H ‐3a,6‐methano‐1,3‐benzoxazol‐3‐yl](oxo)acetaldehyde) was found to react stereoselectively with simple nitro compounds in the presence of Al 2 O 3 or Bu 4 NF⋅3 H 2 O (TBAF) as catalysts, affording the diastereoisomeric nitro alcohols 3 – 6 with good asymmetric induction. When Al 2 O 3 was used, the ( S )‐configuration at the center bearing the OH group was generated, with the relative syn ‐configuration for the major diastereoisomers. In the case of the nitro‐aldol reaction catalyzed by TBAF, an opposite asymmetric induction was found for two nitro compounds. In contrast to 1 , compound 12 (=((4 R ,5 S )‐4‐methyl‐2‐oxo‐5‐phenyl‐1,3‐oxazolidin‐3‐yl)(oxo)acetaldehyde), a derivative of Evans auxiliary, gave rise to poor asymmetric induction in Henry reactions.