Journal of the American Chemical Society 2006-06-07

Catalytic enantioselective aldol reaction to ketones.

Kounosuke Oisaki, Dongbo Zhao, Motomu Kanai, Masakatsu Shibasaki

Index: J. Am. Chem. Soc. 128 , 7164, (2006)

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Abstract

An enantioselective aldol reaction between ketones and ketene silyl acetals is described using CuF-chiral phosphine as a catalyst. The key for high enantioselectivity was the development of a novel ligand derived from Taniaphos combined with the unique accelerative effect of PhBF3K. These conditions are applicable to various substrates such as aromatic, aliphatic, and heteroaromatic ketones. In the case of substituted nucleophiles, the reaction proceeds well. The diastereoselectivity is independent of ketene silyl acetal geometry. This is the first example of a catalytic enantio- and diastereoselective aldol reaction to ketones using ketene silyl acetals.