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. 2016 Apr 5:12:643-7.
doi: 10.3762/bjoc.12.63. eCollection 2016.

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

Sara Meninno  1 , Chiara Volpe  1 , Giorgio Della Sala  1 , Amedeo Capobianco  1 , Alessandra Lattanzi  1
Affiliations

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

Sara Meninno et al. Beilstein J Org Chem. .

Abstract

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.

Keywords: amine thioureas; aymmetric synthesis; cascade reaction; organocatalysis; tetrahydrothiophenes.

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Figures

Scheme 1
Scheme 1
Organocatalysts screened in the cascade reaction.
Scheme 2
Scheme 2
Synthesis of catalyst VIII.
See this image and copyright information in PMC

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