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Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization

Yap, Connor; Lenagh-Snow, Gabriel M.J.; Narayan Karad, Somnath; Lewis, William; Diorazio, Louis J.; Lam, Hon Wai

Authors

Connor Yap

Gabriel M.J. Lenagh-Snow

Somnath Narayan Karad

William Lewis

Louis J. Diorazio

HON LAM Hon.Lam@nottingham.ac.uk
Professor of Sustainable Chemistry



Abstract

Enantioselective nickel-catalyzed arylative cyclizations of substrates containing a Z-allylic phosphate tethered to an alkyne are described. These reactions give multisubstituted chiral aza- and carbocycles, and are initiated by the addition of an arylboronic acid to the alkyne, followed by cyclization of the resulting alkenylnickel species onto the allylic phosphate. The reversible E/Z isomerization of the alkenylnickel species is essential for the success of the reactions.

Citation

Yap, C., Lenagh-Snow, G. M., Narayan Karad, S., Lewis, W., Diorazio, L. J., & Lam, H. W. (in press). Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization. Angewandte Chemie International Edition, 56, https://doi.org/10.1002/anie.201703380

Journal Article Type Article
Acceptance Date May 24, 2017
Online Publication Date Jun 12, 2017
Deposit Date Jun 21, 2017
Publicly Available Date Jun 21, 2017
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 56
DOI https://doi.org/10.1002/anie.201703380
Keywords Allylic substitution; Asymmetric catalysis; Cyclization;
Isomerization; Nickel
Public URL http://eprints.nottingham.ac.uk/id/eprint/43683
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201703380/abstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





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