Alexy, Eric J. and Virgil, Scott C. and Bartberger, Michael D. and Stoltz, Brian M. (2017) Enantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α-Quaternary Ketones. Organic Letters, 19 (19). pp. 5007-5009. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20170914-131404458
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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.
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| 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. | ||||||||||||
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| Issue or Number: | 19 | ||||||||||||
| Record Number: | CaltechAUTHORS:20170914-131404458 | ||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170914-131404458 | ||||||||||||
| Official Citation: | Enantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α-Quaternary Ketones Eric J. Alexy, Scott C. Virgil, Michael D. Bartberger, and Brian M. Stoltz Organic Letters 2017 19 (19), 5007-5009 DOI: 10.1021/acs.orglett.7b02354 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 81444 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||
| Deposited On: | 14 Sep 2017 21:58 | ||||||||||||
| Last Modified: | 09 Mar 2020 13:19 |
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