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

J Am Chem Soc. 2022 Jun 22;144(24):10943-10949. doi: 10.1021/jacs.2c03805. Epub 2022 Jun 8.

Authors

Padmanabha V Kattamuri¹, Jidong Zhao¹, Tamal Kanti Das¹, Juha H Siitonen^{1

2}, Nathan Morgan³, Daniel H Ess³, László Kürti¹

Affiliations

¹ Department of Chemistry, Rice University, Houston, Texas 77030, United States.
² Department of Chemistry and Materials Science, Aalto University, Kemistintie 1, FI-02150 Espoo, Finland.
³ Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States.

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Aziridines* / chemistry
Methylmethacrylates
Molecular Structure
Stereoisomerism

Substances

Aziridines
Methylmethacrylates
Multibond

Grants and funding

R35 GM136373/GM/NIGMS NIH HHS/United States