Generation of (E)-Silylketene Acetals in a Rhodium-DuPhos Catalyzed Two-Step Reductive Aldol Reaction

Cun-Xiang Zhao, Jonathan Bass and James P. Morken

*Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, Email: morkenbc.edu

C.-X. Zhao, J. Bass, J. P. Morken, Org. Lett., 2001, 3, 2839-2842.

DOI: 10.1021/ol016279l

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Abstract

Rh-DuPhos catalyzes an in situ conjugate reduction of an unsaturated carbonyl compound with Cl₂MeSiH to provide an (E)-silylketene acetal. This enolate undergoes a noncatalyzed reaction with a variety of aldehydes to give the derived syn-aldol adducts in high yields and diastereoselection.

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Key Words

Mukaiyama Aldol Reaction, β-hydroxy esters, silanes

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ID: J54-Y2001