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Swern Oxidation of a Hindered β-Hydroxyester

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The highly hindered β-hydroxyester 3 fails to oxidize under the usual Swern reaction conditions, whereas closely related compounds react successfully. Swern oxidation of 3 occurs if the work-up conditions are modified or if diazabicycloundecane (DBU) rather than triethylamine (TEA) is used as the base in the reation. A mechanistic rationale is proposed in which the kinetic acidity of a dimethylsulfoxonium salt derived from 3 is postulated to be suppressed by intramolecular complexation.

Affiliations: 1: Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, U.S.A


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