title: Organocatalytic mannich-type reactions of trifluoroethyl thioesters.
abstract: Direct organocatalytic Mannich-type reactions of thioesters provide for the expedient and diastereoselective synthesis of protected beta-amino acids. A variety of thioesters were found to be reactive with different imines under mild conditions to provide beta-amino acids in good yields. This chemistry was extended to a diastereo- and enantioselective variant.
authors.affiliation: Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Naoto
authors.initials: N
authors.lastname: Utsumi
authors.forename: Shinji
authors.initials: S
authors.lastname: Kitagaki
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D014050:Toluene / Q000737:chemistry
chemical_list: D000596:Amino Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004952:Esters; D007097:Imines; D013438:Sulfhydryl Compounds; D014050:Toluene; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene