Issue 3, 2024

Asymmetric copper-catalyzed alkynylallylic dimethylamination

Abstract

A feasible protocol for Cu-catalyzed asymmetric alkynylallylic dimethylamination is developed with the discovery of tetramethyldiaminomethane as a new, stable and convenient surrogate of dimethylamine. A series of enantioenriched 1,4-enynes are constructed in reasonable yields, high regioselectivities and moderate to good enantioselectivities. Mechanistic experiments show that the tertiary amine works as a nucleophile directly followed by the release of the expected dialkylamine unit, different from the conventional primary and secondary amines with the cleavage of a proton as the nucleophile. DFT calculations elucidate the origin of regio- and enantioselectivity for the present transformation.

Graphical abstract: Asymmetric copper-catalyzed alkynylallylic dimethylamination

Supplementary files

Article information

Article type
Research Article
Submitted
23 Oct 2023
Accepted
04 Dec 2023
First published
05 Dec 2023
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2024,11, 690-695

Asymmetric copper-catalyzed alkynylallylic dimethylamination

S. Luo, G. Lin and Z. He, Org. Chem. Front., 2024, 11, 690 DOI: 10.1039/D3QO01749D

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