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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 Wai Lam



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.

Journal Article Type Article
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 56
APA6 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
DOI https://doi.org/10.1002/anie.201703380
Keywords Allylic substitution; Asymmetric catalysis; Cyclization;
Isomerization; Nickel
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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