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金(I)催化的炔丙基氮丙啶重排反应:三取代和环烯烃稠合吡咯的合成

Au(I)-catalyzed rearrangement reaction of propargylic aziridine: synthesis of trisubstituted and cycloalkene-fused pyrroles.

作者信息

Zhao Xiong, Zhang En, Tu Yong-Qiang, Zhang Yong-Qiang, Yuan Dao-Yi, Cao Ke, Fan Chun-An, Zhang Fu-Min

机构信息

State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.

出版信息

Org Lett. 2009 Sep 3;11(17):4002-4. doi: 10.1021/ol901649p.

Abstract

A rearrangement reaction of propargylic aziridine, catalyzed by PPh(3)AuCl/AgOTf, forming trisubstituted and cycloalkene-fused pyrroles is described which involves an unusual tandem cyclization/ring-opening/Wagner-Meerwein process. The unique structures of the products demonstrated its potential applications for synthesizing structurally diverse alkaloids.

摘要

描述了在三苯基膦金(I)氯化物/三氟甲磺酸银催化下,炔丙基氮杂环丙烷的重排反应,生成三取代和环烯烃稠合的吡咯,该反应涉及一个不寻常的串联环化/开环/瓦格纳-米尔温过程。产物独特的结构表明其在合成结构多样的生物碱方面具有潜在应用。

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