Chemical Biology & Drug Design 2010-08-01

The mimic of type II aldolases chemistry: asymmetric synthesis of beta-hydroxy ketones by direct aldol reaction.

Zhijin Lu, Haibo Mei, Jianlin Han, Yi Pan

Index: Chem. Biol. Drug Des. 76(2) , 181-6, (2010)

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Abstract

An efficient direct aldol reaction has been developed for the synthesis of chiral beta-hydroxy ketone using a combination of C(1)-symmetric chiral prolinamides based on o-phenylenediamine and zinc triflate as catalyst. The reaction was convenient to carry out in aqueous media with up to 98% chemical yields and up to 94% ee values. The current strategy can be regarded as the analogue of aldolase type II, which suggests a new pathway for the designing of new organocatalysts.