Published October 6, 2017
| Version Supplemental Material + Accepted Version
Journal Article
Open
Enantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α-Quaternary Ketones
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1.
California Institute of Technology
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2.
Amgen (United States)
Abstract
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.
Additional Information
© 2017 American Chemical Society. Received: July 30, 2017; Published: September 13, 2017. We thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. E.J.A. is grateful to the National Science Foundation for a predoctoral fellowship. We thank Dr. David VanderVelde (Caltech) for NMR expertise, and Dr. Mona Shahgholi (Caltech) and Naseem Torian (Caltech) for mass spectrometry assistance. The authors declare no competing financial interest.Attached Files
Accepted Version - nihms906117.pdf
Supplemental Material - ol7b02354_si_001.pdf
Supplemental Material - ol7b02354_si_002.pdf
Files
nihms906117.pdf
Additional details
Identifiers
- PMCID
- PMC5632216
- Eprint ID
- 81444
- Resolver ID
- CaltechAUTHORS:20170914-131404458
Funding
- NIH
- R01GM080269
- Amgen
- Gordon and Betty Moore Foundation
- Caltech
- NSF Predoctoral Fellowship
Dates
- Created
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2017-09-14Created from EPrint's datestamp field
- Updated
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2022-03-22Created from EPrint's last_modified field