title: Trisubstituted 2-trifluoromethyl pyrrolidines via catalytic asymmetric Michael addition/reductive cyclization.
abstract: The stereoselective synthesis of trisubstituted 2-trifluoromethyl pyrrolidines by asymmetric Michael addition/hydrogenative cyclization is described. The direct organocatalytic addition of 1,1,1-trifluoromethylketones to nitroolefins proceeds under mild reaction conditions and low catalyst loadings to provide Michael adducts in high yield with excellent diastereo- and enantioselectivity. Catalytic hydrogenation of the Michael adducts stereoselectively generates 2-trifluoromethylated pyrrolidines bearing three contiguous stereocenters. A stereospecific route to epimeric 2-trifluoromethyl pyrrolidines from a common intermediate is described.
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
authors.forename: Michael T
authors.initials: MT
authors.lastname: Corbett
authors.forename: Qihai
authors.initials: Q
authors.lastname: Xu
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006845:Hydrocarbons, Fluorinated; D011759:Pyrrolidines
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