Asymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes†
Chung-Meng Chao,Denis Beltrami,Patrick Y. Toullec,Véronique Michelet
Chemical Communications Pub Date : 10/14/2009 00:00:00 , DOI:10.1039/B913554E
Abstract

The enantioselective asymmetric gold-catalyzed cycloisomerization reactions of heteroatom tethered 1,6-enynes are conducted in the presence of a chiral cationic Au(I) catalyst ((R)-4-MeO-3,5-(t-Bu)2-MeOBIPHEP-(AuCl)2/AgOTf system) in toluene under mild conditions and lead to functionalized bicyclo[4.1.0]heptene derivatives in excellent enantiomeric excesses ranging from 90–98%.

Graphical abstract: Asymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes