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Enamine versus Oxazolidinone: What Controls Stereoselectivity in Proline‐Catalyzed Asymmetric Aldol Reactions?
Author(s) -
Sharma Akhilesh K.,
Sunoj Raghavan B.
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201001588
Subject(s) - enamine , aldol reaction , stereoselectivity , enantioselective synthesis , chemistry , organocatalysis , stereochemistry , catalysis , organic chemistry
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.