Issue 41, 2022

Iminologous epoxide ring-closure


The discovery of new reactions enables chemists to attain a better understanding of fundamental chemical reactivity and push the boundaries of organic synthesis. Our understanding and manipulation of high-energy states such as reactive conformations, intermediates, and transition structures contribute to this field. Herein we interrogate epoxide ring-closure by inserting the C[double bond, length as m-dash]N functionality into a well-known precursor to nucleophilic epoxide ring-closure. The synthesis of tetrasubstituted, nitrile-tethered epoxides takes place via activation of iminologous diols followed by fragmentation. Mechanistic study reveals the transformation to be stereospecific, which is consistent with the concerted nature of the epoxide ring-closure.

Graphical abstract: Iminologous epoxide ring-closure

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Article information

Article type
Edge Article
11 Aug 2022
04 Oct 2022
First published
10 Oct 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 12175-12179

Iminologous epoxide ring-closure

C. Tien, A. J. Lough and A. K. Yudin, Chem. Sci., 2022, 13, 12175 DOI: 10.1039/D2SC04496J

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