title: Chiral biscinchona alkaloid promoted asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones with Morita-Baylis-Hillman carbonates.
abstract: A highly diastereo- and enantioselective asymmetric allylic alkylation reaction with respect to prochiral 3-substituted benzofuran-2(3H)-ones and MBH carbonate by a chiral biscinchona alkaloid catalyst was investigated. The corresponding adducts, containing a quaternary center at the C3-position of the benzofuran-2(3H)-one as well as a vicinal tertiary center, were generally obtained in high yields (up to 97%) with very good diastereo- (up to 98:2 dr) and enantioselectivities (up to 95% ee).
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin, China.
authors.forename: Cong
authors.initials: C
authors.lastname: Liu
authors.forename: Bo-Xuan
authors.initials: BX
authors.lastname: Tan
authors.forename: Jia-Lu
authors.initials: JL
authors.lastname: Jin
authors.forename: Yue-Yan
authors.initials: YY
authors.lastname: Zhang
authors.forename: Nan
authors.initials: N
authors.lastname: Dong
authors.forename: Xin
authors.initials: X
authors.lastname: Li
authors.forename: Jin-Pei
authors.initials: JP
authors.lastname: Cheng
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000498:Allyl Compounds; D001572:Benzofurans