Construction of azacycles by intramolecular amination of organoboronates and organobis(boronates)

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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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Xu, P., Zhang, M., Ingoglia, B., Allais, C., Dechert-Schmitt, A. M. R., Singer, R. A., & Morken, J. P. (2021). Construction of azacycles by intramolecular amination of organoboronates and organobis(boronates). Organic Letters, 23(9), 3379–3383. https://doi.org/10.1021/acs.orglett.1c00856

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