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Synfacts 2007(2): 0178-0178  
DOI: 10.1055/s-2006-958972
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Quaternary (E)-Vinylglycines

Contributor(s): Mark Lautens, Frédéric Ménard
M. C. Jones, S. P. Marsden*, D. M. Muñoz Subtil
University of Leeds, UK
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

Chiral quaternary (E)-vinylglycines can be prepared in two steps from simple aldehydes. The method offers an alternative to those of Seebach and co-workers (Helv. Chim. Acta 1987, 70, 237-261) or Berkowitz and co-workers (J. Org. Chem. 2000, 65, 2907-2918). The dienolate of 2 alkylates the electrophile R2 regioselectively at the α-position, and yields the olefin in the trans geometry only.