Enantioselective Hydroalkenylation of Olefins with Enol Sulfonates Enabled by Dual Copper Hydride and Palladium Catalysis
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nihms-1696061.pdf
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Accepted version
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1.12 MB
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Author(s)
Schuppe, Alexander W
Knippel, James Levi
Borrajo-Calleja, Gustavo M
Buchwald, Stephen L
Date Issued
2021
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Schuppe, Alexander W, Knippel, James Levi, Borrajo-Calleja, Gustavo M and Buchwald, Stephen L. 2021. "Enantioselective Hydroalkenylation of Olefins with Enol Sulfonates Enabled by Dual Copper Hydride and Palladium Catalysis." Journal of the American Chemical Society, 143 (14).
Version
Author's final manuscript
Abstract
The catalytic enantioselective synthesis of α-chiral olefins represents a valuable strategy for rapid generation of structural diversity in divergent syntheses of complex targets. Herein, we report a protocol for the dual CuH- and Pd-catalyzed asymmetric Markovnikov hydroalkenylation of vinyl arenes and the anti-Markovnikov hydroalkenylation of unactivated olefins, in which readily available enol triflates can be utilized as alkenyl coupling partners. This method allowed for the synthesis of diverse α-chiral olefins, including tri- and tetrasubstituted olefin products, which are challenging to prepare by existing approaches.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/JACS.1C02117
