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

Yap, Connor and Lenagh-Snow, Gabriel M.J. and Narayan Karad, Somnath and Lewis, William and Diorazio, Louis J. and Lam, Hon Wai (2017) Enantioselective nickel-catalyzed intramolecular allylic alkenylations enabled by reversible alkenylnickel E/Z isomerization. Angewandte Chemie International Edition, 56 . pp. 8216-8220. ISSN 1521-3773

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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.

Item Type: Article
Keywords: Allylic substitution; Asymmetric catalysis; Cyclization; Isomerization; Nickel
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/anie.201703380
Depositing User: Eprints, Support
Date Deposited: 21 Jun 2017 10:52
Last Modified: 12 Oct 2017 23:57
URI: http://eprints.nottingham.ac.uk/id/eprint/43683

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