title: Organocatalytic asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates.
abstract: The first asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates for the construction of a stereogenic center bearing a unique trifluoromethyl group and a sulfur atom has been achieved in high yields and excellent enantioselectivities with a 1 mol % bifunctional organocatalyst. Subsequent transformation led to the expedient preparation of enantioenriched thiochroman-4-one and the key intermediate of the potent inhibitor of MMP-3, (R)-γ-trifluoromethyl γ-sulfone hydroxamate.
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, 430072, China.
authors.forename: Xiu-Qin
authors.initials: XQ
authors.lastname: Dong
authors.forename: Xin
authors.initials: X
authors.lastname: Fang
authors.forename: Chun-Jiang
authors.initials: CJ
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D003437:Crotonates / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D061965:Matrix Metalloproteinase Inhibitors; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
chemical_list: D003437:Crotonates; D004791:Enzyme Inhibitors; D061965:Matrix Metalloproteinase Inhibitors; D013438:Sulfhydryl Compounds; D005461:Fluorine; D013455:Sulfur