Brønsted acid catalysis of achiral enamine for regio-and enantioselective nitroso aldol synthesis

N Momiyama, H Yamamoto

Index: Momiyama, Norie; Yamamoto, Hisashi Journal of the American Chemical Society, 2005 , vol. 127, # 4 p. 1080 - 1081

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Citation Number: 228

Abstract

Two types of chiral Brønsted acid catalysts have been shown to catalyze regio-and enantioselective nitroso aldol synthesis between nitrosobenzene and achiral enamine. The combination of Brønsted acidity and amine moiety of enamine realizes complete regioselectivity with high enantioselectivity. After a survey of Brønsted acid catalysts, 1- naphthyl glycolic acid is found to be optimal in the O-nitroso aldol pathway, while 1- ...