Journal
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS
Volume 33, Issue -, Pages 83-108Publisher
ELSEVIER
DOI: 10.1016/j.jphotochemrev.2017.10.002
Keywords
Photocycloadditions; Oxetanes; Reaction mechanism; Stereoselectivity; Organic synthesis
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The [2+2] photocycloaddition between an electronically excited carbonyl compound and an alkene leading to oxetanes (Paterno-Buchi reaction) is one of the most investigated organic photochemical reaction. Regio-, stereo- and site selectivities are discussed as a consequence of the reaction mechanism. Spin multiplicity and electron transfer have a significant impact on the outcome of the reaction. Typical carbonyl and alkene reaction partners are presented indicating scope and limitation of the reaction. The Paterno-Buchi reaction possesses particular interest for being applied to organic synthesis, considering the difficulty for non-photochemical reactions to obtain oxetanes, with or without stereoselectivity. Mechanistic details are particularly focused. It has been applied as key step in various multi-step syntheses. (C) 2017 Elsevier B.V. All rights reserved.
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