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Enantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic ?-Quaternary Ketones.

ABSTRACT: A catalytic, enantioselective decarboxylative allylic alkylation of 4-thiopyranones is reported. The ?-quaternary 4-thiopyranones produced are challenging to access by standard enolate alkylation owing to facile ring-opening ?-sulfur elimination. In addition, reduction of the carbon-sulfur bonds provides access to elusive acyclic ?-quaternary ketones. The alkylated products are obtained in up to 92% yield and 94% enantiomeric excess.

SUBMITTER: Alexy EJ 

PROVIDER: S-EPMC5632216 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Enantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α-Quaternary Ketones.

Alexy Eric J EJ   Virgil Scott C SC   Bartberger Michael D MD   Stoltz Brian M BM  

Organic letters 20170913 19

A 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. ...[more]

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