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Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids
Journal article

Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids

Hongming Li, Baomin Wang and Li Deng
Journal of the American Chemical Society, Vol.37(3), pp.732-no
06/06/2006
PMID: 16417358

Abstract

Esters - chemistry Ketones - chemical synthesis Stereoisomerism Ketones - chemistry Nitro Compounds - chemistry Nitro Compounds - chemical synthesis Catalysis Cinchona Alkaloids - chemistry Esters - chemical synthesis Aldehydes - chemistry
The alkaloids (I) and (II) are used to catalyze the reaction of nitromethane with α-ketoesters. In both cases, the corresponding products (with opposite absolute stereochemistry) are formed in excellent yields and enantioselectivities. (Va) and (IXa) are applied for the preparation of (X) and (XI), key intermediates in the synthesis of antitumor and anti-HIV natural products.

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