title: An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C-C bond cleavage of epoxides: highly efficient synthesis of chiral furan derivatives.
abstract: An efficient enantioselective [3+2] cycloaddition of alkynes with oxiranes via selective C-C bond cleavage of epoxides was developed. A number of optically active 2,5-dihydrofurans were obtained in excellent yields (up to 99%) and enantioselectivities (up to 95% ee) under mild reaction conditions. Moreover, chiral tetrahydrofuran could also be obtained by cycloaddition of alkene and oxirane or hydrogenation of chiral 2,5-dihydrofuran.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. xmfeng@scu.edu.cn.
authors.forename: Weiliang
authors.initials: W
authors.lastname: Chen
authors.forename: Xuan
authors.initials: X
authors.lastname: Fu
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiao
authors.initials: X
authors.lastname: Yuan
authors.forename: Weiwei
authors.initials: W
authors.lastname: Luo
authors.forename: Juhua
authors.initials: J
authors.lastname: Feng
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D004852:Epoxy Compounds / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006865:Hydrogenation; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D004852:Epoxy Compounds; D005663:Furans; C018674:tetrahydrofuran; D002244:Carbon