Highly Enantioselective Synthesis of α-Amino Acid Derivatives by an NHC-Catalyzed Intermolecular Stetter Reaction

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‐unsu...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 50; no. 6; pp. 1410 - 1414
Main Authors Jousseaume, Thierry, Wurz, Nathalie E., Glorius, Frank
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 07.02.2011
WILEY‐VCH Verlag
Wiley
Subjects
amino acids
Amino Acids - chemical synthesis
Amino Acids - chemistry
asymmetric catalysis
Catalysis
Chemistry
Chemistry, Multidisciplinary
Heterocyclic Compounds - chemistry
Methane - analogs & derivatives
Methane - chemistry
N-heterocyclic carbene
organocatalysis
Physical Sciences
protonation
Science & Technology
Stereoisomerism
N-heterocyclic carbene
protonation
ASYMMETRIC-SYNTHESIS
HYDROGEN-ATOM TRANSFER
ENOLATE PROTONATIONS
amino acids
ALDEHYDES
asymmetric catalysis
CONJUGATE ADDITION-PROTONATION
CASCADE REACTION
organocatalysis
NONADJACENT STEREOCENTERS
1,4-ADDITION/ENANTIOSELECTIVE PROTONATION
ACTIVATED DOUBLE-BONDS
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Summary: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.
Bibliography:Deutsche Telekom Stiftung
ark:/67375/WNG-J8N7NL4G-N
ArticleID:ANIE201006548
We thank the Deutsche Telekom Stiftung (N.E.W.) for generous support, Isabel Piel for the preparation of catalyst 3 and for helpful comments, and Karin Gottschalk for technical assistance. The research of F.G. has been supported by the Alfried Krupp Prize for Young University Teachers of the Alfried Krupp von Bohlen und Halbach Foundation. NHC=N-heterocyclic carbene.
Alfried Krupp von Bohlen und Halbach Foundation
istex:8FD6E9374F1B06AEDE951550B665137F1D4CC1AB
We thank the Deutsche Telekom Stiftung (N.E.W.) for generous support, Isabel Piel for the preparation of catalyst
and for helpful comments, and Karin Gottschalk for technical assistance. The research of F.G. has been supported by the Alfried Krupp Prize for Young University Teachers of the Alfried Krupp von Bohlen und Halbach Foundation. NHC=N‐heterocyclic carbene.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201006548