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Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene–ketones

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Abstract

The enantioselective nickel-catalyzed reaction of tethered allene–ketones with (hetero)arylboronic acids or potassium vinyltrifluoroborate is described. Carbonickelation of the allene gives allylnickel species, which undergo cyclization by 1,2-allylation to produce chiral tertiary-alcohol-containing aza- and carbocycles in high diastereo- and enantioselectivities.

Graphical abstract: Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene–ketones

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Article information


Submitted
16 Oct 2019
Accepted
20 Jan 2020
First published
21 Jan 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene–ketones

R. Di Sanza, T. L. N. Nguyen, N. Iqbal, S. P. Argent, W. Lewis and H. W. Lam, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC05246A

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