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Synfacts 2008(2): 0175-0175
DOI: 10.1055/s-2007-992488
DOI: 10.1055/s-2007-992488
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Lewis Acid Mediated Addition of Silyl Ketene Imines to Aldehydes
S. E. Denmark*, T. W. Wilson, M. T. Burk, Jr. J. R. Heemstra,
University of Illinois, Urbana, USA
Further Information
Publication History
Publication Date:
23 January 2008 (online)
Significance
A novel method for creating quaternary carbon centers is demonstrated using a SiCl4/bisphosphoramide-catalyzed aldol reaction between silyl ketene imines and aldehydes. Substituents on the silyl ketene imine are limited to unbranched alkyl or aryl species for high enantioselectivities. The scope of substituents on the aldehyde is broad, although the reaction is limited to aromatic aldehydes.