Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes
Name
jacs.9b07582.pdf
Description
Published version
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1007.63 KB
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Adobe PDF
Checksum (MD5)
f88f737549f72d47ebc465b1c9b5a169
Author(s)
Bayeh-Romero, Liela
Buchwald, Stephen Leffler
Date Issued
August 2019
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Bayeh-Romero, Liela and Stephen L. Buchwald. "Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes." Journal of the American Chemical Society 141, 35 (August 2019): 13788-13794 © 2019 American Chemical Society
Version
Final published version
Abstract
The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride catalyzed semireduction of conjugated enynes to furnish 1,3-disubstituted allenes using water as the proton source. This protocol is sufficiently mild to accommodate an assortment of functional groups including keto, ester, amino, halo, and hydroxyl groups. Additionally, applications of this method for the selective synthesis of monodeuterated allenes and chiral 2,5-dihydropyrroles are described.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-NonCommercial-NoDerivs License
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DOI of Published Version
https://doi.org/10.1021/jacs.9b07582
