Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation |
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| Authors: | Al-Rashid Ziyad F Hsung Richard P |
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| Affiliation: | Division of Pharmaceutical Sciences and Department of Chemistry, Rennebohm Hall 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705-2222, USA. |
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| Abstract: | 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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