Enantioselective Hydrocarbamoylation of Alkenes
Name
Angew Chem Int Ed - 2022 - Feng - Enantioselective Hydrocarbamoylation of Alkenes.pdf
Description
Published version
Size
4.7 MB
Format
Adobe PDF
Checksum (MD5)
c6c710cdb455dd7b4fd5fc302be15841
Author(s)
Feng, Sheng
Dong, Yuyang
Buchwald, Stephen L
Date Issued
August 2022
Journal
Angewandte Chemie International Edition
Publisher
Wiley
Citation
Feng, Sheng, Dong, Yuyang and Buchwald, Stephen L. 2022. "Enantioselective Hydrocarbamoylation of Alkenes." Angewandte Chemie International Edition, 61 (31).
Version
Final published version
Abstract
The asymmetric hydroaminocarbonylation of olefins represents a straightforward approach for the synthesis of enantioenriched amides, but is hampered by the necessity to employ CO gas, often at elevated pressures. We herein describe, as an alternative, an enantioselective hydrocarbamoylation of alkenes leveraging dual copper hydride and palladium catalysis to enable the use of readily available carbamoyl chlorides as a practical carbamoylating reagent. The protocol is applicable to various types of olefins, including alkenyl arenes, terminal alkenes, and 1,1-disubstituted alkenes. Substrates containing a diverse range of functional groups as well as heterocyclic substructures undergo functionalization to provide α- and β-chiral amides in good yields and with excellent enantioselectivities.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-NonCommercial-NoDerivs License
Persistent DSpace Link
DOI of Published Version
10.1002/anie.202206692
