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July 1, 2002Journal of the American Chemical Society68 citations

Highly Diastereoselective Dioxetane Formation in the Photooxygenation of Enecarbamates with an Oxazolidinone Chiral Auxiliary: Steric Control in the 2 + 2 Cycloaddition of Singlet Oxygen through Conformational Alignment

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WAWaldemar AdamSBSara G. BosioNTNicholas J. Turro

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Abstract

The photooxygenation of oxazolidinone-substituted enecarbamates leads to diastereomerically pure dioxetanes. The high diastereoselectivity is rationalized in terms of effective pi-facial control achieved by shielding one side of the double bond with the chiral auxiliary. The absolute configuration of the dioxetanes is assigned by derivatization to diols.

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Adam et al. (2002) studied this question.

synapsesocial.com/papers/6a9cc4a944c4a4ef85b67f45https://doi.org/10.1021/ja026815k
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