Asymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes.
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%.
Chao
Chung-Meng
CM
Laboratoire Charles Friedel, Ecole Nationale Supérieure de Chimie de Paris UMR 7223, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.
Beltrami
Denis
D
Toullec
Patrick Y
PY
Michelet
Véronique
V
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D013237:Stereoisomerism; D014050:Toluene / Q000737:chemistry
D001643:Bridged Bicyclo Compounds; D014050:Toluene; D006046:Gold