Recent advances in the ring expansion of cyclobutanols, oxetanols, and azetidinols
File(s)
Accepted version
Author(s)
Natho, Philipp
Allen, Lewis AT
Parsons, Philip J
Type
Journal Article
Abstract
The number of developed methodologies for the ring expansion of cyclobutanol rings to five, six and seven-membered rings has increased significantly over the last six years. In this timeframe, the semipinacol rearrangement of vinyl-group containing cyclobutanols to cyclopentanones has been advanced under photoredox and electrochemical conditions, enabling the concomitant introduction of a wide array of functional groups. The expansion to 1- and 4-tetralones has been achieved for the first time under transition-metal-free conditions and even expansion to seven-membered rings has been demonstrated under rhodium catalysis. In this article, we will critically discuss the scope, application and mechanistic studies of procedures published since 2013, and provide a short outlook on the emerging potential for further development in this area.
Date Issued
2020-04-02
Date Acceptance
2020-01-30
Citation
Tetrahedron Letters, 2020, 61 (14), pp.1-9
ISSN
0040-4039
Publisher
Elsevier BV
Start Page
1
End Page
9
Journal / Book Title
Tetrahedron Letters
Volume
61
Issue
14
Copyright Statement
© 2020 Elsevier Ltd. All rights reserved. This manuscript is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International Licence http://creativecommons.org/licenses/by-nc-nd/4.0/
Sponsor
Imperial College Trust
Identifier
https://www.sciencedirect.com/science/article/pii/S0040403920301180
Grant Number
N/A
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
Ring expansion
Semipinacol rearrangement
Photochemistry
Electrochemistry
VISIBLE-LIGHT PHOTOREDOX
MIGRATION SEQUENCES
BRONSTED ACID
REARRANGEMENT
CATALYSIS
CYCLOPENTANONES
ALKENYLCYCLOBUTANOLS
CONSTRUCTION
ACCESS
0304 Medicinal and Biomolecular Chemistry
0305 Organic Chemistry
Organic Chemistry
Publication Status
Published
Article Number
151695
Date Publish Online
2020-01-31