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Stereoselective Photooxidations by the Schenck Ene Reaction
Author(s) -
Bayer Patrick,
PérezRuiz Raúl,
Jacobi von Wangelin Axel
Publication year - 2018
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201800058
Subject(s) - ene reaction , singlet oxygen , allylic rearrangement , chemistry , stereoselectivity , context (archaeology) , catalysis , atom economy , combinatorial chemistry , molecule , organic synthesis , oxygen , photochemistry , organic chemistry , paleontology , biology
150 years after the first report of an organic reaction with singlet oxygen ( 1 O 2 ) and 70 years after the discovery of the singlet oxygen‐ene reaction (Schenck reaction) with alkenes, this allylic photooxidation has matured to a powerful transformation that enables access to diverse sets of allyl alcohol derivatives from ubiquitous starting materials. The reaction exhibits high sustainability (100 % atom economy, use of simple alkenes, air, metal‐free catalyst and visible light). Good levels of chemo‐, regio‐, and stereocontrol were observed in the synthesis of various fine chemical building blocks and biologically active molecules. This Minireview provides an overview of the key strategies that enable stereoselective oxygen‐ene reactions in the context of complex molecule syntheses including photo‐oxygenations of functionalized alkenes, cycloalkenes, and auxiliary‐based methods.