期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 7, 期 -, 页码 1021-1029出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.116
关键词
asymmetric catalysis; bicycloheptene; cycloisomerization reactions; enynes; gold
资金
- Centre National de la Recherche Scientifique
- Ministere de l'Education et de la Recherche [2006-2009]
- National Research Agency [ANR-09-JCJC-0078, 2009-2012]
- Agence Nationale de la Recherche (ANR) [ANR-09-JCJC-0078] Funding Source: Agence Nationale de la Recherche (ANR)
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 AgNTf2) 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%.
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