A highly diastereoselective decarboxylative mannich reaction of β-keto acids with optically active N-sulfinyl α-imino esters.
A range of protected γ-oxo-α-amino esters have been prepared in a highly regio- and stereoselective manner through the decarboxylative Mannich reaction of β-keto acids with optically active N-tert-butanesulfinyl α-imino esters in the presence of 3 mol % La(OTf)(3) or 5 mol % Y(OTf)(3) at 20 °C. Preliminary mechanistic studies indicate that the reaction proceeds through imine addition followed by decarboxylation.
Joint Laboratory of Green Synthetic Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.
Cui-Feng
CF
Yang
Chen
C
Shen
Jian-Yong
JY
Wang
Shi-Kai
SK
Tian
D004952:Esters / Q000737:chemistry*; D007651:Keto Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
D004952:Esters; D007651:Keto Acids; D013452:Sulfonium Compounds