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Download fileEnantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α‑Quaternary Ketones
journal contribution
posted on 2017-09-13, 13:51 authored by Eric J. Alexy, Scott C. Virgil, Michael D. Bartberger, Brian M. StoltzA catalytic, enantioselective
decarboxylative allylic alkylation
of 4-thiopyranones is reported. The α-quaternary 4-thiopyranones
produced are challenging to access by standard enolate alkylation
owing to facile ring-opening β-sulfur elimination. In addition,
reduction of the carbon–sulfur bonds provides access to elusive
acyclic α-quaternary ketones. The alkylated products are obtained
in up to 92% yield and 94% enantiomeric excess.
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alkylated productsAccessenantioselective decarboxylative allylic alkylation4- thiopyranonesaccessThiopyranoneenantiomericacyclic α- quaternary ketonesα- quaternary 4- thiopyranonesKetonering-opening β- sulfur eliminationQuaternaryAcyclicEnantioselective Pd-Catalyzed Decarboxylative Allylic AlkylationStereogenicenolate alkylationbond