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

Published on 2017-09-14T12:48:57Z (GMT) by
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.

Cite this collection

Alexy, Eric J.; Virgil, Scott C.; Bartberger, Michael D.; Stoltz, Brian M. (2017): Enantioselective Pd-Catalyzed Decarboxylative Allylic

Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α‑Quaternary

Ketones. ACS Publications.

https://doi.org/10.1021/acs.orglett.7b02354

Retrieved: 09:30, Nov 23, 2017 (GMT)