4‐π‐Photocyclization: Scope and Synthetic Applications. Issue 10 (21st October 2019)

• Record Type: Journal Article
• Authors: Coote, Susannah C.
• Other Names: Masson Géraldine guestEditor.; König Burkhard guestEditor.; Yoon Tehshik guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 10(2020)
• Page Start: 1405
• Page End: 1423
• Publication Date: 2019-10-21
• Subjects: Cyclization -- Electrocyclic reactions -- Photochemistry -- Cyclobutene -- Pericyclic reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901230
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : This minireview highlights the scope of 4‐π‐photocyclizations (photoinduced electrocyclizations that involve 4 pi electrons and generate bicyclic cyclobutenes from 1, 3‐dienes), including an overview of the historical progressions as well as recent developments. A range of 1, 3‐diene substrates is covered, including cycloheptatrienes, tropones, tropolones, cyclic 1, 3‐dienes, 2‐pyrones, 2‐pyridones, pyrimidines, 1, 2‐dihydropyridines, and 1, 2‐dihydro‐pyridazines. The bicyclic cyclobutene products formed through the photocyclizations are highly versatile synthetic intermediates, and examples of the application of these building blocks in the context of synthetic methodology development, natural product synthesis, medicinal chemistry and materials chemistry are featured throughout. Abstract : 4‐π‐Photocyclizations (also referred to a valence isomerizations) allow the generation of versatile bicyclic cyclobutene building blocks from a range of 1, 3‐dienes in a totally atom‐economical process. Herein, the historical developments and recent innovations in 4‐π‐photocyclizations are reviewed, illustrated by applications of these intriguing reactions in total synthesis, medicinal chemistry, and materials chemistry.