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
收藏
页码：8219 / 8223
页数：5
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