Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates
Name
Buchwald_Enantioselective.pdf
Size
2.47 MB
Format
Adobe PDF
Checksum (MD5)
5c69b52d1e7a888a1c00401e35d655fa
Author(s)
Zhou, Yujing
Bandar, Jeffrey
Buchwald, Stephen Leffler
Date Issued
June 2017
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zhou, Yujing et al. “Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.” Journal of the American Chemical Society 139, 24 (June 2017): 8126–8129 © 2017 American Chemical Society
Version
Author's final manuscript
Abstract
The direct asymmetric copper hydride (CuH)-catalyzed coupling of α,β-unsaturated carboxylic acids to aryl alkenes to access chiral α-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which significantly expands the range of accessible products compared with existing hydroacylation methodology. Although mechanistic studies are ongoing, we propose that CuH-catalyzed silylation of unsaturated acids occurs to access a uniquely effective acyl electrophilic coupling partner.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/JACS.7B04937
