Issue 2, 2022

Elucidating the selectivity of dyotropic rearrangements of β-lactones: a computational survey

Abstract

The dyotropic rearrangement of β-lactones is a neglected treasure in the family of multi-bond reactions and pericyclic reactions. Despite its appealing synthetic potential, the complicated migration selectivity greatly limits its widespread application. In this work, we report the first systematic and comprehensive computational study on the dyotropic rearrangements of β-lactones. The use of the double-hybrid functional ensures the accuracy of results. On the basis of the present study and our previous work, five methods to control the reaction selectivity of dyotropic rearrangements of β-lactones have been summarized, providing valuable references for synthetic chemists to design and develop brand-new type dyotropic reactions.

Graphical abstract: Elucidating the selectivity of dyotropic rearrangements of β-lactones: a computational survey

Supplementary files

Article information

Article type
Research Article
Submitted
22 Oct 2021
Accepted
23 Nov 2021
First published
25 Nov 2021

Org. Chem. Front., 2022,9, 329-341

Elucidating the selectivity of dyotropic rearrangements of β-lactones: a computational survey

J. Zhang, Y. Ma, K. Qiu, B. Li, Z. Xue, B. Tian and Y. Tang, Org. Chem. Front., 2022, 9, 329 DOI: 10.1039/D1QO01591E

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