Highly enantioselective synthesis of naphthoquinones and pyranonaphthoquinones catalyzed by bifunctional chiral bis-squaramides†,10.1039/C5OB00105F

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Highly enantioselective synthesis of naphthoquinones and pyranonaphthoquinones catalyzed by bifunctional chiral bis-squaramides†

Nagaraju Molleti

Organic & Biomolecular Chemistry Pub Date : 03/23/2015 00:00:00 , DOI:10.1039/C5OB00105F

Abstract

A variety of enantioenriched naphthoquinones have been synthesized in high yields and excellent enantioselectivities (up to >99% ee) using a bifunctional chiral bis-squaramide catalyzed conjugate addition of 2-hydroxy-1,4-naphthoquinone to 2-enoylpyridines. Some of the Michael products have been successfully converted into various enantioenriched pyranonaphthoquinone derivatives. The protocol is further extended to the synthesis of various 4-hydroxycoumarin derivatives under mild conditions.