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Deracemization of Quaternary Stereocenters by Pd‐Catalyzed Enantioconvergent Decarboxylative Allylation of Racemic β‐Ketoesters
Author(s) -
Mohr Justin T.,
Behenna Douglas C.,
Harned Andrew M.,
Stoltz Brian M.
Publication year - 2005
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.200502018
Subject(s) - stereocenter , chemistry , stereoselectivity , catalysis , quaternary carbon , stereochemistry , enantioselective synthesis , organic chemistry , combinatorial chemistry
Stereochemical alchemy! Racemic allyl β‐ketoesters allow the regiocontrolled formation of enolates, where the same catalyst is intimately involved in both the stereoablative (CC bond‐breaking) and stereoselective (CC bond‐forming) steps. This mechanistic and practical insight led to the formation of multiple quaternary carbon stereocenters in a single cascade reaction (see scheme).