Abstract
β'-Thio-substituted-enones, assembled from the combination of β-tert-butylthio-substituted aldehydes and alkynes, using rhodium catalysis, are shown to smoothly undergo in situ intramolecular S-conjugate addition to deliver a range of S-heterocycles in a one-pot process. Aryl, alkenyl, and alkyl aldehydes can all be employed, to provide thiochroman-4-ones, hexahydro-4H-thiochromen-4-ones, and tetrahydrothiopyran-4-ones, respectively. A variety of in situ oxidations are also performed, allowing access to S,S-dioxide derivatives, as well as unsaturated variants.
Highlights
R ecent years have seen the emergence of alkene and alkyne hydroacylation reactions as useful methods for the synthesis of ketones and enones, respectively.[1]
Our approach is shown in Scheme 1b and involves chelate-controlled alkyne hydroacylation followed by an acid triggered thio-conjugate addition.[17]
Encouraging precedent is provided from our own reports of hydroquinolone synthesis,7c and Stanley’s chroman-4-one chemistry,[15] both of these sequences are limited to aryl aldehyde substrates, constraining the structural variation accessible in the products
Summary
R ecent years have seen the emergence of alkene and alkyne hydroacylation reactions as useful methods for the synthesis of ketones and enones, respectively.[1]. Our approach is shown in Scheme 1b and involves chelate-controlled alkyne hydroacylation followed by an acid triggered thio-conjugate addition.[17] encouraging precedent is provided from our own reports of hydroquinolone synthesis,7c and Stanley’s chroman-4-one chemistry,[15] both of these sequences are limited to aryl aldehyde substrates, constraining the structural variation accessible in the products.
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