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Organocatalytic Michael Addition of Naphthoquinone with α,β-Unsaturated Ketones: Primary Amine Catalyzed Asymmetric Synthesis of Lapachol Analogues

✍ Scribed by Guangcun Zhang; Yifeng Wang; Wei Zhang; Xiangsheng Xu; Aiguo Zhong; Danqian Xu

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 443 KB
Volume: 2011
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201001570

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✦ Synopsis

Abstract

A highly efficient organocatalytic synthesis of lapachol analogues from the Michael addition of naphthoquinone to various α,β‐unsaturated ketones catalyzed by primary amines is presented. Good to high yields (up to 93 %) and high to excellent enantioselectivities (up to 98 % ee) were obtained for the target compounds. MS (ESI) provided evidence for the key intermediates in the proposed mechanism.

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