Work

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

Year: 2021

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.1c02117

Authors: Alexander W. Schuppe, James Levi Knippel, Gustavo M. Borrajo-Calleja, Stephen L. Buchwald

Institution: Massachusetts Institute of Technology

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Arnold and Mabel Beckman Foundation, Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung, National Institute of General Medical Sciences, Division of Graduate Education

Awards: G236542531, Enantio- and Regioselective Synthesis of Amides and Sulfonamides by Cu-Catalyzed Hydrofunctionalization of Alkenes, G5662436926, Late Transition Metal Catalysts for Organic Synthesis, Metal-Catalyzed Methods for Organic Synthesis