Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade

被引：28

作者：

Brandstaetter, Marco ^{[1
]}

Huwyler, Nikolas ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Lab Organ Chem, HCI H335, Vladimir Prelog Weg 3, CH-8093 Zurich, Switzerland

来源：

CHEMICAL SCIENCE | 2019年 / 10卷 / 35期

关键词：

BENT ACYCLIC ALLENE; GOLD CATALYSIS; EFFICIENT SYNTHESIS; ENYNYL ACETATES; ALDOL REACTION; TANDEM; COMPLEXES; CARBODICARBENE; ACCESS; ESTERS;

D O I：

10.1039/c9sc02828e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereoselective synthesis of bicyclo[3.3.0]octenones from chiral 1,3-enyne aldehydes bearing propargylic acetates is described. The method is based on a Au(i)-catalyzed domino sequence with concomitant transfer of chirality involving 1,3-acyloxy migration followed by Nazarov cyclization and an unprecedented aldol addition. The method furnishes densely functionalized bicyclic structures in high yields, with up to 97% ee and good diastereoselectivity.

引用

页码：8219 / 8223

页数：5

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