Bicyclic Aziridinium Ions in Azaheterocyclic Chemistry – Preparation and Synthetic Application of 1‐Azoniabicyclo[n.1.0]alkanes

Abstract

AbstractRecent advances in the field of ring‐expansion chemistry, involving 1‐azoniabicyclo[n.1.0]alkane scaffolds (bicyclic aziridinium ions) as key transient intermediates, have made it possible to efficiently construct a broad variety of medium‐ and large‐sized functionalized nitrogen‐containing heterocycles. In this tutorial review, a comprehensive survey of all pathways leading to the generation of 1‐azoniabicyclo[n.1.0]alkanes is provided, as well as a discussion on their subsequent ring expansions to relevant azaheterocycles governed by ring size, substitution pattern, and/or nature of applied nucleophiles.magnified image