Catalytic asymmetric conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones with bifunctional catalysts.
In this communication, we describe an unprecedented highly enantioselective catalytic conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones catalyzed by acid-base bifunctional catalysis. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds that are otherwise difficult to prepare by asymmetric catalysis. The successful development of this reaction resulted from a discovery that, upon proper modification, a cinchona alkaloid bearing a thiourea functionality at 6' position can afford highly efficient catalysis for asymmetric conjugate additions.
Liu
Yan
Y
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Sun
Bingfeng
B
Wang
Baomin
B
Wakem
Matthew
M
Deng
Li
L
D000215:Acylation; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D002930:Cinchona Alkaloids; D004952:Esters; D023303:Oxazolidinones; D013438:Sulfhydryl Compounds