Published July 2, 2020
| Accepted Version + Supplemental Material
Journal Article
Open
Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones
Abstract
Herein, we report the palladium-catalyzed decarboxylative asymmetric allylic alkylation of α-enaminones. In addition to serving as valuable synthetic building blocks, we exploit the α-enaminone scaffold and its derivatives as probes to highlight structural and electronic factors that govern enantioselectivity in this asymmetric alkylation reaction. Utilizing the (S)-t-BuPHOX ligand in a variety of nonpolar solvents, the alkylated products are obtained in up to 99% yield and 99% enantiomeric excess.
Additional Information
© 2020 American Chemical Society. Received: April 25, 2020; Published: June 16, 2020. We thank the NIH-NIGMS (R01GM080269), and the NSF (predoctoral research fellowship to D.C.D., No. DGE-1144469) for financial support. Research reported in this publication was supported by the NIH-NIGMS under Award Number F32GM116304 (postdoctoral fellowship to J. T. Moore). We further thank Dr. Scott C. Virgil (Caltech) for assistance with chiral-SFC separation and insightful discussion. The authors declare no competing financial interest.Attached Files
Accepted Version - nihms-1637399.pdf
Supplemental Material - ol0c01441_si_001.pdf
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ol0c01441_si_001.pdf
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Additional details
- PMCID
- PMC7608880
- Eprint ID
- 103952
- DOI
- 10.1021/acs.orglett.0c01441
- Resolver ID
- CaltechAUTHORS:20200622-104137176
- R01GM080269
- NIH
- DGE-1144469
- NSF Graduate Research Fellowship
- F32GM116304
- NIH Postdoctoral Fellowship
- Created
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2020-06-23Created from EPrint's datestamp field
- Updated
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2022-02-15Created from EPrint's last_modified field