Dual Strain-Release Cascade for Accessing sp 3 -Rich Azetidine–Bicyclopentane Frameworks Bearing Multiple Quaternary Carbon Centers

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Authors: Vinjamuri Srinivasu, Ajmeera Balaraju, Nakka Ashok Chinni Kumar, Devarajulu Sureshkumar
Cited by: 2
References: 30

Abstract

Azetidines and bicyclopentanes (BCPs) have emerged as valuable bioisosteres for pyridine and benzene rings, driving considerable interest in modern medicinal chemistry. Here, we report a photocatalytic strategy for the efficient and selective functionalization of azabicyclo[1.1.0]butanes (ABBs) and bicyclobutanes (BCBs), enabling direct access to saturated cyclic and bicyclic scaffolds under mild, environmentally benign conditions. The method demonstrates broad functional-group compatibility and accommodates extensive structural diversity. This strain-release approach significantly enhances synthetic flexibility, allowing a wide range of ABBs to undergo controlled ring-opening transformations to afford densely substituted azetidine-BCP architectures bearing three all-carbon quaternary centers, a structural motif that remains challenging to construct using conventional synthetic approaches.

Fields of Study & Subjects

Radical Photochemical Reactions Synthesis and Catalytic Reactions Cyclopropane Reaction Mechanisms

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
12
Pages
3856–3861
Publication date
16 March 2026
Language
EN