Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation

Organic Letters
Ziyad F Al-Rashid, Richard P Hsung

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.

References

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Citations

May 1, 2010·Chemical Reviews·Kyle A DeKorverRichard P Hsung
Oct 22, 2008·The Journal of Organic Chemistry·Ziyad F Al-RashidKang Zhao
May 5, 2010·Organic Letters·Biplab BanerjeeSteven L Castle
May 25, 2013·Journal of the American Chemical Society·Renhe LiuWeiping Tang
Apr 15, 2014·The Journal of Organic Chemistry·Peng ZhangChristian Wolf
Sep 23, 2010·Chemistry : a European Journal·Sabrina OuizemAlejandro Pérez-Luna
Mar 18, 2016·Organic Letters·Michiko SasakiKei Takeda
Apr 1, 2010·Angewandte Chemie·Gwilherm EvanoKévin Jouvin
Jun 19, 2015·Tetrahedron Letters·Andrea M Cook, Christian Wolf
Sep 11, 2010·Chemical Communications : Chem Comm·Paul W DaviesNicolas Martin
Jul 8, 2014·Journal of the American Chemical Society·Joshua S Alford, Huw M L Davies
Nov 29, 2017·Organic & Biomolecular Chemistry·Xin LiuLong-Wu Ye
Feb 13, 2014·Chemical Communications : Chem Comm·Andrea M Cook, Christian Wolf
Nov 8, 2020·Nature Communications·Linwei ZengSunliang Cui
Nov 11, 2008·The Journal of Organic Chemistry·Karin DooleweerdtTroels Skrydstrup
Nov 28, 2008·Organic Letters·Karin DooleweerdtTroels Skrydstrup
Oct 30, 2010·Organic Letters·Alexandre PradalVeronique Michelet

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