CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes
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nihms936029.pdf
Description
Accepted version
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830.81 KB
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Author(s)
Zhou, Yujing
Bandar, Jeffrey
Liu, Richard
Buchwald, Stephen Leffler
Date Issued
January 2018
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zhou, Yujing et al. “CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes.” Journal of the American Chemical Society, vol. 140, no. 2, 2018, pp. 606-609 © 2018 The Author(s)
Version
Author's final manuscript
Abstract
The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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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.
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DOI of Published Version
https://doi.org/10.1021/JACS.7B12260
