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

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

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 cyclizat...

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Bibliographic Details
Main Authors: Yap, Connor, Lenagh-Snow, Gabriel M.J., Narayan Karad, Somnath, Lewis, William, Diorazio, Louis J., Lam, Hon Wai
Format: Article
Published: Wiley-VCH Verlag 2017
Subjects:
Allylic substitution; Asymmetric catalysis; Cyclization; Isomerization; Nickel
Online Access:https://eprints.nottingham.ac.uk/43683/
Description
Summary: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.

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