Download PDF
Synfacts 2010(5): 0568-0568  
DOI: 10.1055/s-0029-1219705
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Multicomponent Asymmetric Synthesis of γ-Hydroxy Ketones

Contributor(s): Mark Lautens, Jane Panteleev
X.-Y Guan, L.-P. Yang, W. Hu*
East China Normal University, Shanghai, P. R. of China
Further Information

Publication History

Publication Date:
22 April 2010 (online)

    Permissions and Reprints

Significance

This work outlines a multicomponent reaction between a diazoacetate, water, and an α,β-unsaturated ketone. Diazoacetate reacts with water to generate oxonium ylides, which have been reacted with aldehydes and imines previously, but this is reportedly the first example of a reaction with a Michael acceptor. The transformation yields γ-hydroxy ketones with contiguous quaternary and trisubstituted stereocenters.