铂催化的1,5-二炔基酯的串联重排反应：异常的区域选择性1,5-氢迁移

Platinum-Catalyzed Cascade Rearrangement Reaction of 1,5-Diynyl Esters: Unusual Regioselective 1,5-Hydride Migration.

作者信息

Zhu Hui, Huang Jiapian, Fan Congbin, Chen Zhiyuan

机构信息

Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry&Chemical Engineering, Jiangxi Normal University, Ziyang Road 99, Nanchang, Jiangxi, 330022, P. R. China.

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, 330013, P. R. China).

出版信息

Chem Asian J. 2015 Jul;10(7):1463-6. doi: 10.1002/asia.201500236. Epub 2015 May 27.

DOI:10.1002/asia.201500236

PMID:25929800

Abstract

A highly regioselective sequential 1,3-acyloxy migration/pentannulation/1,5-hydride migration reaction is disclosed which provides an efficient access to (E)-2-vinyl-3-oxo-1-methyleneindenes under neutral and mild reaction conditions. The migrated hydrogen atom was derived from an unactivated alkyl group, and the long-range 1,5-H shift was confirmed through related deuterium experiments.

摘要

公开了一种高度区域选择性的顺序1,3-酰氧基迁移/戊环化/1,5-氢化物迁移反应，该反应在中性温和的反应条件下提供了一种有效合成(E)-2-乙烯基-3-氧代-1-亚甲基茚的方法。迁移的氢原子来源于未活化的烷基，并且通过相关的氘实验证实了远程1,5-H迁移。