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.
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.
see article for more examples
Mukaiyama Aldol Reaction, β-hydroxy esters, silanes