Aza-Quasi-Favorskii Reaction: Construction of Highly Substituted Aziridines through a Concerted Multibond Rearrangement Process

Padmanabha V. Kattamuri, Jidong Zhao, Tamal Kanti Das, Juha H. Siitonen, Nathan Morgan, Daniel H. Ess, László Kürti

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

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.

Original languageEnglish
Pages (from-to)10943-10949
Number of pages7
JournalJournal of the American Chemical Society
Volume144
Issue number24
DOIs
StatePublished - 22 Jun 2022
Externally publishedYes

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