Issue 9, 2022
From the journal:

Organic Chemistry Frontiers

Mechanism and origins of enantioselectivity of cobalt-catalyzed intermolecular hydroacylation/cyclization of 1,6-enynes with aldehydes†

Jiaao Ge,a   Hongli Wu,a   Deping Konga  and  Genping Huang ORCID logo *a  

* Corresponding authors

a Department of Chemistry, School of Science and Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, Tianjin 300072, P. R. China
E-mail: gphuang@tju.edu.cn
Web: https://www.x-mol.com/groups/gphuang

Abstract

Density functional theory calculations were performed to investigate the cobalt-catalyzed intermolecular hydroacylation/cyclization of 1,6-enynes with aldehydes. The computations show that the initial oxidative cyclization constitutes the rate-determining step of the overall reaction. The enantioselectivity is caused by the competition between the oxidative cyclization of the S-pathway and the migratory insertion of the R-pathway. The origins of the enantioselectivity are mainly due to the steric repulsion between the aldehyde moiety and the aryl substituent of the 1,6-enyne.

Graphical abstract: Mechanism and origins of enantioselectivity of cobalt-catalyzed intermolecular hydroacylation/cyclization of 1,6-enynes with aldehydes

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Article information

DOI
https://doi.org/10.1039/D2QO00179A
Article type
Research Article
Submitted
03 Feb 2022
Accepted
15 Mar 2022
First published
15 Mar 2022

Org. Chem. Front., 2022,9, 2368-2374

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Mechanism and origins of enantioselectivity of cobalt-catalyzed intermolecular hydroacylation/cyclization of 1,6-enynes with aldehydes

J. Ge, H. Wu, D. Kong and G. Huang, Org. Chem. Front., 2022, 9, 2368 DOI: 10.1039/D2QO00179A

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