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Two-Component Assembly of Thiochroman-4-ones and Tetrahydrothiopyran-4-ones Using a Rhodium-Catalyzed Alkyne Hydroacylation/Thio-Conjugate-Addition Sequence

Ana´s Bouisseau, John Glancy and Michael C. Willis*

*Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U.K., Email: michael.willischem.ox.ac.uk

A. Bouisseau, J. Glancy, M. C. Willis, Org. Lett., 2016, 18, 5676-5679.

DOI: 10.1021/acs.orglett.6b02909 (free Supporting Information)


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Abstract

A Rh-catalyzed reaction of β-tert-butylthio-substituted aldehydes and alkynes provides β′-thio-substituted-enones, that smoothly undergo in situ intramolecular S-conjugate addition to deliver a range of S-heterocycles in a one-pot process. Various in situ oxidations are also performed, allowing access to S,S-dioxide derivatives, as well as unsaturated variants.

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Key Words

thioflavanones


ID: J54-Y2016