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Reactive Intermediates from DMDO Oxidation of Ynamides. Trapping of a de novo Chiral Push−Pull Carbene via Cyclopropanation

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posted on 2008-02-21, 00:00 authored by Ziyad F. Al-Rashid, Richard P. Hsung
The reaction profile of DMDO oxidations of ynamides is described. This work illustrates the first examples of highly diastereoselective intramolecular cyclopropanations of a push−pull carbene derived from alkyne oxidation. In addition, the ynamide oxidation provides facile access to ketoimides and reveals mechanistic insights into the chemistry of electronically biased oxirenes.

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