title: Catalytic asymmetric 1,6-Michael addition of arylthiols to 3-methyl-4-nitro-5-alkenyl-isoxazoles with bifunctional catalysts.
abstract: An enantioselective 1,6-Michael addition reaction of arylthiols to a wide range of 3-methyl-4-nitro-5-alkenyl-isoxazoles catalyzed by readily available Takemoto's thiourea catalyst has been developed. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds bearing a 4-nitroisoxazol-5-yl moiety in high to excellent yields (up to 97%) and high enantioselectivities (up to 91% ee). Significantly, the potential utilities of the protocol had been further demonstrated by gram-scale reaction and the versatile conversions of some resulting products into other functionalized and useful compounds.
authors.affiliation: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Qing-Lan
authors.initials: QL
authors.lastname: Pei
authors.forename: Hong-Wei
authors.initials: HW
authors.lastname: Sun
authors.forename: Zhi-Jun
authors.initials: ZJ
authors.lastname: Wu
authors.forename: Xi-Lin
authors.initials: XL
authors.lastname: Du
authors.forename: Xiao-Mei
authors.initials: XM
authors.lastname: Zhang
authors.forename: Wei-Cheng
authors.initials: WC
authors.lastname: Yuan
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D007555:Isoxazoles / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry
chemical_list: D000475:Alkenes; D007555:Isoxazoles; D013438:Sulfhydryl Compounds; D013890:Thiourea