Enamine versus Oxazolidinone: What Controls Stereoselectivity in Proline-Catalyzed Asymmetric Aldol Reactions

Take the right path: Comparison of the oxazolidinone and enamine pathways in enantioselective aldol reactions by using density functional and ab initio transition states reveals that the oxazolidinone route does not provide the correct stereochemical outcome (see picture), whereas the enamine pathwa...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 49; no. 36; pp. 6373 - 6377
Main Authors Sharma, Akhilesh K, Sunoj, Raghavan B
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 23.08.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Subjects
Aldehydes - chemistry
aldol reaction
Catalysis
density functional calculations
diastereoselectivity
Molecular Conformation
organocatalysis
Oxazolidinones - chemistry
Proline - chemistry
reaction mechanisms
Stereoisomerism
Thermodynamics
Online AccessGet full text

Cover

More Information
Summary:Take the right path: Comparison of the oxazolidinone and enamine pathways in enantioselective aldol reactions by using density functional and ab initio transition states reveals that the oxazolidinone route does not provide the correct stereochemical outcome (see picture), whereas the enamine pathway predicts the correct stereoselectivity.
Bibliography:http://dx.doi.org/10.1002/anie.201001588
istex:9B0AE66AFB533E6D99F81289D734EDF526FFBE58
ark:/67375/WNG-T25WBT7Q-K
ArticleID:ANIE201001588
CSIR
We thank IIT Bombay computer center and CMSD Hyderabad for generous computing time. A.K.S. is grateful to CSIR New Delhi for a senior research fellowship.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201001588