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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Published inBeilstein journal of organic chemistry Vol. 12; no. 1; pp. 643 - 647
Main Authors Meninno, Sara, Volpe, Chiara, Della Sala, Giorgio, Capobianco, Amedeo, Lattanzi, Alessandra
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 05.04.2016
Beilstein-Institut
Subjects
amine thioureas
aymmetric synthesis
cascade reaction
Chemistry
Letter
organocatalysis
tetrahydrothiophenes
organocatalysis
amine thioureas
aymmetric synthesis
cascade reaction
tetrahydrothiophenes
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.63