A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes

Author(s)
Tsai, Erica Y.; Liu, Richard; Yang, Yang; Buchwald, Stephen Leffler
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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
Date issued
2018-02
URI
https://hdl.handle.net/1721.1/125456
Department
Massachusetts Institute of Technology. Department of Chemistry
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
ISSN
0002-7863
1520-5126
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