Organocatalytic mannich-type reactions of trifluoroethyl thioesters.
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.
Utsumi
Naoto
N
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.
Kitagaki
Shinji
S
Barbas
Carlos F
CF
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
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