Synfacts 2008(2): 0175-0175  
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

Contributor(s): Mark Lautens, Praew Thansandote
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)


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.