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Org Lett. 2003 Dec 25;5(26):4951-3.

Stereochemical features of the physical and chemical interactions of singlet oxygen with enecarbamates.

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Department of Chemistry and Department of Chemical Engineering, Columbia University, 3000 Broadway, Mail Code 3119, New York, NY 10027, USA.


Oxazolidinone-substituted enecarbamates represent a mechanistically rich system for the study of stereoelectronic, steric, and conformational effects on stereoselectivity and mode selectivity in (1)O(2) [2 + 2] and ene reactions. Photooxygenation of these enecarbamates with (1)O(2) leads to diastereomerically pure dioxetanes that decompose to yield an oxazolidinone carbaldehyde and one of the two enantiomers of methyldesoxybenzoin in enantiomeric excess. Stereoselectivity originates at the allylic stereocenter, a result supported by quenching studies, computational analysis, and deuterium solvent isotope effects. [reaction: see text].


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