Stereoselective Photooxidations by the Schenck Ene Reaction. Issue 7 (29th May 2018)

• Record Type: Journal Article
• Authors: Bayer, Patrick; Pérez‐Ruiz, Raúl; Jacobi von Wangelin, Axel
• Is Part Of: ChemPhotoChem. Volume 2:Issue 7(2018)
• Page Start: 559
• Page End: 570
• Publication Date: 2018-05-29
• Subjects: hydroperoxides -- photocatalysis -- photooxidation -- Schenck ene reaction -- singlet oxygen -- stereoselectivity; Photochemistry -- Periodicals; Periodicals; Electronic journals; 541.35
• DOI: 10.1002/cptc.201800058
• Languages: English
• ISSNs: 2367-0932

Abstract

Abstract: 150 years after the first report of an organic reaction with singlet oxygen ( 1 O2 ) 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. Abstract : It′s all under control : The singlet oxygen‐ene reaction (Schenck reaction) has matured to a powerful transformation that enables access to diverse allyl alcohols from ubiquitous starting materials. The reaction exhibits high sustainability (100 % atom economy, use of simple alkenes, air, a metal‐free catalyst, visible light) and chemo‐, regio‐ and stereocontrol. This Minireview provides an overview of key strategies that enable stereoselective reactions in complex molecule syntheses.