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Highly Enantioselective Synthesis of α‐Amino Acid Derivatives by an NHC‐Catalyzed Intermolecular Stetter Reaction
Author(s) -
Jousseaume Thierry,
Wurz Nathalie E.,
Glorius Frank
Publication year - 2011
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.201006548
Subject(s) - intramolecular force , protonation , enantioselective synthesis , intermolecular force , carbene , chemistry , catalysis , stereoselectivity , michael reaction , organocatalysis , combinatorial chemistry , organic chemistry , medicinal chemistry , molecule , ion
PROTONtype : An NHC‐catalyzed (NHC=N‐heterocyclic carbene), highly asymmetric intermolecular Stetter reaction allows the atom‐economic and efficient formation of valuable α‐amino acid derivatives (see scheme); the key step is an intramolecular stereoselective protonation. For the first time, a β‐unsubstituted Michael acceptor was employed successfully in this kind of reaction, most importantly, with a broad range of different aldehydes.