Catalytic, enantioselective aldol additions to ketones

SE Denmark, Y Fan

Index: Denmark, Scott E.; Fan, Yu Journal of the American Chemical Society, 2002 , vol. 124, # 16 p. 4233 - 4235

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Citation Number: 189

Abstract

Catalytic, enantioselective additions of a trichlorosilyl ketene acetal to ketones have been demonstrated. The trichlorosilyl enolate of methyl acetate undergoes a rapid and high- yielding aldol addition to a wide range of ketones (aromatic, olefinic, acetylenic, aliphatic) in the presence of a catalytic amount of pyridine N-oxide. Moreover, in the presence of a catalytic amount (10 mol%) of a chiral bispyridine bis N-oxide (possessing both axial and ...