Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere

被引：192

作者：

Chiba, Shunsuke ^{[1
]}

Zhang, Line ^{[1
]}

Lee, Jian-Yuan ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Math & Phys Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 21期

关键词：

CARBON TRIPLE BOND; MOLECULAR-OXYGEN; OXIDATIVE AMIDATION; CLEAVAGE; DIOXYGEN; COMPLEXES; MONOOXYGENASES; TRANSFORMATION; ACTIVATION; REACTIVITY;

D O I：

10.1021/ja1027327

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A copper-catalyzed reaction of alpha-azido-N-arylamides was found to proceed under an oxygen atmosphere to afford azaspirocyclohexadienones. The present transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from alpha-azido-N-arylamides and their imino-cupration with an intramolecular benzene ring on the amido nitrogen followed by consecutive formation of C=O bonds. The preliminary investigation revealed that molecular oxygen is a prerequisite for achieving the present catalytic cyclization and that one of the oxygen atoms of O(2) was found to be incorporated into the cyclohexadienone moiety.

引用

页码：7266 / +

页数：3

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