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

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