Construction of Azacycles by Intramolecular Amination of Organoboronates and Organobis(boronates)

Intramolecular amination of organoboronates occurs with a 1,2-metalate shift of an aminoboron ate complex to form azetidines, pyrrolidines, and piperidines. Bis(boronates) undergo site-selective amination to form boronate-containing azacycles. Enantiomerically enriched azacycles are formed with high stereospecificity.

Automated summary

Intramolecular amination of organoboronates results in the formation of various nitrogen-containing heterocycles, including azetidines, pyrrolidines, and piperidines. Site-selective amination of bis(boronates) leads to the formation of boronate-containing azacycles. Chiral azacycles are formed with high stereospecificity.