Gold-Catalyzed Addition of Propargyl Acetates to Olefins via O-Acyl Migration/Cyclopropanation Sequence: Insight into the Diastereoselective Formation of the Alkene

被引：3

作者：

Barbazanges, Marion ^{[1
]}

Gimbert, Yves ^{[1
,2
]}

Fensterbank, Louis ^{[1
]}

机构：

[1] Sorbonne Univ, Inst Parisien Chim Mol, CNRS, UMR 8232, F-75252 Paris, France

[2] Univ Grenoble Alpes, Dept Chim Mol, CNRS, UMR 5250, F-38050 Grenoble, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 05期

关键词：

CYCLOISOMERIZATION; ESTERS; CYCLIZATION; MIGRATION; CYCLOPROPANATION; EFFICIENT;

D O I：

10.1021/acs.joc.2c02623

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This article discloses a study on the well-known addition of propargyl acetates to olefins via an O-acyl migration/ cyclopropanation sequence. Herein, we show that the stereochemical outcome of the olefin is strongly dependent on the gold catalyst and reaction parameters (concentration, temperature, and alkene partner equivalents); the E- and Z-isomers can be selectively formed by the judicious choice of reaction conditions.

引用

页码：3297 / 3302

页数：6