Synfacts 2011(4): 0446-0446  
DOI: 10.1055/s-0030-1259610
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

NHC-Catalyzed Intermolecular Stetter Reaction with Asymmetric Protonation

Contributor(s): Benjamin List, Steffen Müller
T. Jousseaume, N. E. Wurz, F. Glorius*
Universität Münster, Germany
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Publication History

Publication Date:
18 March 2011 (online)


The Glorius group reports an ­intermolecular Stetter reaction between different aldehydes and N-acylamido acrylate catalyzed by the NHC derived from 1. The desired products, α-chiral amino acid derivatives, are obtained in high yields and high enantioselectivities for a broad scope of aldehydes. The observed enantio­selectivity arises from the stereoselective protonation of the Michael adduct rather than from the prior C-C bond-forming event. The authors propose that the chiral catalyst forces the Michael addition to proceed with a well-defined geometry, setting the stage for the construction of the desired stereocenter by the intramolecular protonation. An alternative concerted mechanism can also not be ruled out as mentioned by the authors.