title: Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene.
abstract: A comprehensive study on the asymmetric gold-catalyzed cycloisomerization reaction of heteroatom tethered 1,6-enynes is described. The cycloisomerization reactions were conducted in the presence of the chiral cationic Au(I) catalyst consisting of (R)-4-MeO-3,5-(t-Bu)(2)-MeOBIPHEP-(AuCl)(2) complex and silver salts (AgOTf or AgNTf(2)) in toluene under mild conditions to afford functionalized bicyclo[4.1.0]heptene derivatives. The reaction conditions were found to be highly substrate-dependent, the best results being obtained in the case of oxygen-tethered enynes. The formation of bicyclic derivatives, including cyclopropyl pentasubstituted ones, was reported in moderate to good yields and in enantiomeric excesses up to 99%.
authors.affiliation: Laboratoire Charles Friedel, UMR 7223, Ecole Nationale Supérieure de Chimie de Paris, Chimie ParisTech, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Pradal
authors.forename: Chung-Meng
authors.initials: CM
authors.lastname: Chao
authors.forename: Patrick Y
authors.initials: PY
authors.lastname: Toullec
authors.forename: Véronique
authors.initials: V
authors.lastname: Michelet