Enantioselective Hydroalkenylation of Olefins with Enol Sulfonates Enabled by Dual Copper Hydride and Palladium Catalysis

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...

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Main Authors: Schuppe, Alexander W (Author), Knippel, James Levi (Author), Borrajo-Calleja, Gustavo M (Author), Buchwald, Stephen L (Author)
Format: Article
Language:English
Published: American Chemical Society (ACS), 2022-04-25T17:43:14Z.
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Online Access:Get fulltext
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042 |a dc 
100 1 0 |a Schuppe, Alexander W  |e author 
700 1 0 |a Knippel, James Levi  |e author 
700 1 0 |a Borrajo-Calleja, Gustavo M  |e author 
700 1 0 |a Buchwald, Stephen L  |e author 
245 0 0 |a Enantioselective Hydroalkenylation of Olefins with Enol Sulfonates Enabled by Dual Copper Hydride and Palladium Catalysis 
260 |b American Chemical Society (ACS),   |c 2022-04-25T17:43:14Z. 
856 |z Get fulltext  |u https://hdl.handle.net/1721.1/142064 
520 |a 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. 
546 |a en 
655 7 |a Article 
773 |t 10.1021/JACS.1C02117 
773 |t Journal of the American Chemical Society