N‑Heterocyclic Carbene-Catalyzed Atom-Economical and Enantioselective Construction of the C–S Bond: Asymmetric Synthesis of Functionalized Thiochromans

An N-heterocyclic carbene-catalyzed cleavage and recombination of the C–S bond was developed. This is an efficient example of NHC reacting with an unsaturated thioester to generate an α,β-unsaturated acyl azolium with high atom economy. This protocol affords an alternative route for the construction...

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Bibliographic Details
Published inACS catalysis Vol. 7; no. 11; pp. 7797 - 7802
Main Authors Lu, Hong, Zhang, Jia-Lu, Liu, Jin-Yu, Li, Hong-Yu, Xu, Peng-Fei
Format Journal Article
LanguageEnglish
Published American Chemical Society 03.11.2017
Subjects
sulfa-Michael addition
asymmetric synthesis
α,β-unsaturated acyl azolium
thiochroman derivatives
N-heterocyclic carbenes
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Summary:An N-heterocyclic carbene-catalyzed cleavage and recombination of the C–S bond was developed. This is an efficient example of NHC reacting with an unsaturated thioester to generate an α,β-unsaturated acyl azolium with high atom economy. This protocol affords an alternative route for the construction of highly functionalized thiochroman derivatives with three consecutive stereogenic centers with good to high yields, as well as excellent diastereoselectivity and enantioselectivity.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.7b02651