Journal
TETRAHEDRON
Volume 62, Issue 46, Pages 10660-10675Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.07.106
Keywords
singlet oxygen; ene reactions; stereoselectivity; electronic effects; solvent effects
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The factors that control the stereochemistry of sensitized photooxygenation of alkenes via singlet oxygen (ene reaction) are selectively reported. We also introduce our most recent stereoelectronic effects on the singlet oxygen-ene reaction. The origin of site selectivity and solvent-dependent stereoselectivity in this classical ene reaction with simple as well as functionalized alkenes is highlighted. These studies and other similar studies have enhanced substantially the utility of singlet oxygen in the synthesis of natural and non-natural products. (c) 2006 Published by Elsevier Ltd.
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