Catalytic, asymmetric Michael reactions of cyclic diketones with beta,gamma-unsaturated alpha-ketoesters.
Newly synthesized cinchona alkaloid-derived pyrimidines function as effective asymmetric catalysts for the Michael reaction between cyclic diketones and beta,gamma-unsaturated alpha-ketoesters. The reactions of electrophiles with either aryl or alkyl gamma-substituents give 64-99% yields and 94-99% ee.
Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459, USA. mcalter@wesleyan.edu
Michael A
MA
Calter
Jun
J
Wang
D002384:Catalysis; D002930:Cinchona Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011743:Pyrimidines / Q000737:chemistry; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D004952:Esters; D007659:Ketones; D011743:Pyrimidines; C030986:pyrimidine