Published in
American Chemical Society, Organic Letters, 11(7), p. 2089-2092, 2005
DOI: 10.1021/ol0502230
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Stereoselective Photooxidation of Enecarbamates: Reactivity of Ozone vs Singlet Oxygen
Journal article published in 2005 by
J. Sivaguru 
,
Hideaki Saito,
Thomas Poon,
Toma Omonuwa,
Roberto Franz,
Steffen Jockusch,
Catherine Hooper,
Yoshihisa Inoue,
Waldemar Adam,
Nicholas J. Turro
,
Hideaki Saito,
Thomas Poon,
Toma Omonuwa,
Roberto Franz,
Steffen Jockusch,
Catherine Hooper,
Yoshihisa Inoue,
Waldemar Adam,
Nicholas J. Turro
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Abstract
[reaction: see text]. Oxazolidinone-functionalized enecarbamates show contrasting behavior upon oxidation by singlet oxygen and by ozone. The observed stereoselectivity difference indicates that the oxidation with ozone is subject to classic steric effects, whereas the very high selectivity in the photooxidation with singlet oxygen is derived from vibrational deactivation.