Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter

Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter

An investigation on the stereoselective cascade sulfa-Michael/aldol reaction of nitroalkenes and commercially available 1,4-dithiane-2,5-diol to 3,4,5-substituted tetrahydrothiophenes, bearing a quaternary stereocenter, is presented. A secondary amine thiourea derived from (R,R)-1,2-diphenylethylami...

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Bibliographic Details
Main Authors: Sara Meninno, Chiara Volpe, Giorgio Della Sala, Amedeo Capobianco, Alessandra Lattanzi
Format: Article
Language:English
Published: Beilstein-Institut 2016-04-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
cascade reaction
tetrahydrothiophenes
aymmetric synthesis
amine thioureas
organocatalysis
Online Access:https://doi.org/10.3762/bjoc.12.63
Description
Summary:An investigation on the stereoselective cascade sulfa-Michael/aldol reaction of nitroalkenes and commercially available 1,4-dithiane-2,5-diol to 3,4,5-substituted tetrahydrothiophenes, bearing a quaternary stereocenter, is presented. A secondary amine thiourea derived from (R,R)-1,2-diphenylethylamine was found to be the most effective catalyst when using trans-β-methyl-β-nitrostyrenes affording the heterocyclic products in good yields and moderate stereoselectivities.
ISSN:1860-5397

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