Calcium-catalyzed diastereo- and enantioselective 1,4-addition of glycine derivatives to alpha,beta-unsaturated esters.
The first highly diastereo- and enantioselective catalytic asymmetric 1,4-addition reactions of a glycine Schiff base to beta-substituted alpha,beta-unsaturated esters have been developed. The reaction pathway was successfully controlled, and the desired 1,4-addition products were exclusively obtained with high enantioselectivities. The product obtained was converted to a 3-substituted glutamic acid derivative by acid hydrolysis.
Kobayashi
Shū
S
Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. shu_kobayashi@chem.s.u-tokyo.ac.jp
Tsubogo
Tetsu
T
Saito
Susumu
S
Yamashita
Yasuhiro
Y
D002118:Calcium / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D018698:Glutamic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D013237:Stereoisomerism
D004952:Esters; D018698:Glutamic Acid; D002118:Calcium; D005998:Glycine