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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
23 January 2008 (online)
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.