Strain-Release-Driven exo -Cyclization of Bicyclo[1.1.0]butyl Ketones Promoted by Brønsted Acids to Access 2,3-Diazabicyclo[3.1.1]heptenes

Organic Letters 2026

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Authors: Lihang Cao, Junjie Ge, Yi Hua, Xiaoze Bao, Zhikun Yang, Hong Wang, Hua Chen
DOI: 10.1021/acs.orglett.5c04933
Cited by: 2
References: 64

Abstract

-cyclization of bicyclo[1.1.0]butyl ketones with hydrazines has been established. This approach enables efficient ring expansion, leading to a diverse range of 2,3-diazabicyclo[3.1.1]heptenes. Mechanistic studies reveal that the carbonyl group is pivotal, fulfilling a dual role as both the reactive center and a latent activating group. Moreover, the unique dual nucleophilic character of hydrazines, featuring two nitrogen-based nucleophilic sites, is crucial to the success of this transformation.

Fields of Study & Subjects

Cyclopropane Reaction Mechanisms Radical Photochemical Reactions Synthetic Organic Chemistry Methods

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
6
Pages
1947–1952
Publication date
29 January 2026
Language
EN