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Recent advances in the ring expansion of cyclobutanols, oxetanols, and azetidinols

Authors
  • Natho, P
  • Allen, LAT
  • Parsons, PJ
Publication Date
Jan 30, 2020
Source
Spiral - Imperial College Digital Repository
Keywords
Language
English
License
Unknown

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.

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