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

Peilin Xu,Mingkai Zhang,Bryan T. Ingoglia,C. Allais,Anne-Marie R. Dechert-Schmitt,R. Singer,J. Morken

Published 2021 in Organic Letters

ABSTRACT

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.

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