A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes
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Description
Accepted version
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401.97 KB
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Author(s)
Tsai, Erica Y.
Liu, Richard
Yang, Yang
Buchwald, Stephen Leffler
Date Issued
February 2018
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Tsai, Erica Y. et al. "A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes." Journal of the American Chemical Society 140, 6 (February 2018): 2007–2011 © 2018 American Chemical Society.
Version
Author's final manuscript
Abstract
We report a method for the highly enantioselective CuH-catalyzed allylation of ketones that employs terminal allenes as allylmetal surrogates. Ketones and allenes bearing diverse and sensitive functional groups are efficiently coupled with high stereoselectivity and exclusive branched regioselectivity. In stoichiometric experiments, each elementary step of the proposed hydrocupration-addition-metathesis mechanism can be followed by NMR spectroscopy. Keywords: Allenes; Ketones; Nuclear magnetic resonance spectroscopy; Allyl group; Allylation
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.7b12271
