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Synfacts 2011(2): 0177-0177  
DOI: 10.1055/s-0030-1259261
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Lewis Base Catalyzed Asymmetric Aldol Addition of Oxyketene Imines to Aldehydes

Contributor(s): Hisashi Yamamoto, Patrick Brady
S. E. Denmark*, T. W. Wilson
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

The authors developed a practical synthesis of isolable N-silyl oxyketene imines A, which are acyl anion equivalents derived from protected cyanohydrins. Using the chiral Lewis base catalyzed SiCl4-mediated system, these nucleophiles undergo aldol addition to aldehydes to generate β-hydroxy cyanohydrins B in high yield and excellent selectivity.