<i>Aza</i>-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process
Padmanabha V. Kattamuri, Jidong Zhao, Tamal Das, Juha H. Siitonen, Nathan Morgan, Daniel H. Ess, László Kürti
Abstract
A new molecular rearrangement, the aza-Quasi-Favorskii rearrangement, has been developed for the construction of highly substituted aziridines. Electron-deficient O-sulfonyl oximes react readily with α,α-disubstituted acetophenone-derived enolates to furnish highly substituted aziridines via this unprecedented domino process. In-depth computational studies reveal an asynchronous yet concerted nitrenoid-type rearrangement pathway.
Topics & Concepts
ChemistryAcetophenoneSigmatropic reactionCope rearrangementSulfonylPericyclic reactionConcerted reactionAziridineComputational chemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryRing (chemistry)CatalysisAlkylSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques