Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides.
A novel highly enantioselective one-pot dithiolation through sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides catalysed by squaramide has been developed. This organocatalysed reaction proceeded well in high to excellent yields (up to >99%) to afford useful bioactive β-sulfated thioester derivatives with high enantioselectivities (up to 96% ee).
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China. dudm@bit.edu.cn.
Bo-Liang
BL
Zhao
Da-Ming
DM
Du
D000215:Acylation; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D013388:Succinimides; D013438:Sulfhydryl Compounds