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 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...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 12; no. 10; pp. 1585 - 1594
Main Authors Zhao, Bo-Liang, Du, Da-Ming
Format Journal Article
LanguageEnglish
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
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Summary: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 afford useful bioactive beta-sulfated thioester derivatives with high enantioselectivities (up to 96% ee).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/c3ob42137f