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

Zhang, Jingyang and Ma, Yumiao and Qiu, Ke and Li, Bo and Xue, Zhengwen and Tian, Boxue and Tang, Yefeng (2022) Elucidating the selectivity of dyotropic rearrangements of β-lactones: a computational survey. Organic Chemistry Frontiers, 9 (2). pp. 329-341. ISSN 2052-4129. doi:10.1039/d1qo01591e. https://resolver.caltech.edu/CaltechAUTHORS:20211207-6259000

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/D1QO01591EDOIArticle
ORCID:
AuthorORCID
Li, Bo0000-0002-8019-8891
Tian, Boxue0000-0002-5830-0669
Tang, Yefeng0000-0002-6223-0608
Additional Information:© the Partner Organisations 2021. Submitted 22 Oct 2021. Accepted 23 Nov 2021. First published 25 Nov 2021. We acknowledge the financial support from the National Natural Science Foundation of China (21772109 and 21971140), the Beijing Natural Science Foundation (M21011) and the Tsinghua-Peking University Center for Life Sciences (No. 61020100120). We also thank Prof. Dr Chanjuan Xi, Mr Jinlei Yang and Mr Jiekang Tian for their helpful discussion. There are no conflicts to declare.
Funders:
Funding AgencyGrant Number
National Natural Science Foundation of China21772109
National Natural Science Foundation of China21971140
Natural Science Foundation of Beijing MunicipalityM21011
Tsinghua-Peking University61020100120
Issue or Number:2
DOI:10.1039/d1qo01591e
Record Number:CaltechAUTHORS:20211207-6259000
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20211207-6259000
Official Citation:Elucidating the selectivity of dyotropic rearrangements of β-lactones: a computational survey. Org. Chem. Front., 2022, 9, 329-341; DOI: 10.1039/d1qo01591e
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:112267
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:08 Dec 2021 18:03
Last Modified:18 Jan 2022 23:18

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