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

doi:10.1021/jacs.2c03805

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

Rice University
Brigham Young University

Research output: Contribution to journal › Article › Scientific › peer-review

13 Citations (Scopus)

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 language	English
Pages (from-to)	10943-10949
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	144
Issue number	24
DOIs	https://doi.org/10.1021/jacs.2c03805
Publication status	Published - 22 Jun 2022
MoE publication type	A1 Journal article-refereed

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10.1021/jacs.2c03805

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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.",

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AU - Kattamuri, Padmanabha V.

AU - Zhao, Jidong

AU - Das, Tamal Kanti

AU - Siitonen, Juha H.

AU - Morgan, Nathan

AU - Ess, Daniel H.

AU - Kürti, László

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Y1 - 2022/6/22

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AB - 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.

UR - https://www.scopus.com/pages/publications/85132453506

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DO - 10.1021/jacs.2c03805

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AN - SCOPUS:85132453506

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JF - Journal of the American Chemical Society

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ER -

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

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