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Iminologous epoxide ring-closure

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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… Click to show full abstract

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 Created by potrace 1.16, written by Peter Selinger 2001-2019 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.

Keywords: 320 320; epoxide ring; ring closure; iminologous epoxide

Journal Title: Chemical Science
Year Published: 2022

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