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通过钪催化的亲电胺化反应实现 2-萘酚的直接不对称去芳构化。

Direct asymmetric dearomatization of 2-naphthols by scandium-catalyzed electrophilic amination.

机构信息

Key Laboratory of Synthetic and Natural Functional Molecular Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710069 (China).

出版信息

Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2356-60. doi: 10.1002/anie.201409565. Epub 2015 Jan 7.

Abstract

Catalytic asymmetric aminative dearomatization of 1-substituted 2-naphthols was successfully implemented with electrophilic azodicarboxylates under the catalysis of chiral Sc(III)/pybox complexes. This intermolecular reaction represents a hitherto unknown enantioselective C-N bond-forming process through direct dearomatization of phenolic compounds to generate chiral nitrogen-containing quaternary carbon stereocenters.

摘要

手性 Sc(III)/pybox 配合物催化下,芳基重氮二羧酸酯作为亲电试剂,成功实现了 1-取代 2-萘酚的不对称氨基去芳构化反应。该分子间反应代表了一种前所未知的对映选择性 C-N 键形成过程,通过酚类化合物的直接去芳构化,生成手性含氮季碳中心。

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