Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition/thioesterification of thiols with α,β-unsaturated N-acylated succinimides

• Published in: Organic & biomolecular chemistry Vol. 12; no. 10; pp. 1585 - 1594
• Main Authors: Zhao, Bo-Liang, Du, Da-Ming
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 14.03.2014
• Subjects: Acylation; Amides - chemistry; Catalysis; Chemistry; Chemistry, Organic; Molecular Structure; Physical Sciences; Science & Technology; Stereoisomerism; Succinimides - chemistry; Sulfhydryl Compounds - chemical synthesis; Sulfhydryl Compounds - chemistry; COMPLEX; ASYMMETRIC CONJUGATE ADDITION; CHALCONES; NITROALKANES; OXAZOLIDIN-2-ONES; DERIVATIVES; DYNAMIC KINETIC RESOLUTION; HIGHLY EFFICIENT; NITROMETHANE

A novel highly enantioselective one-pot dithiolation through sulfa-Michael addition/thioesterification of thiols with alpha,beta-unsaturated N-acylated succinimides catalysed by squaramide has been developed. This organocatalysed reaction proceeded well in high to excellent yields (up to >99%) to...