Construction of Azacycles by Intramolecular Amination of Organoboronates and Organobis(boronates).
Peilin XuMingkai ZhangBryan IngogliaChristophe AllaisAnne-Marie R Dechert-SchmittRobert A SingerJames P MorkenPublished in: Organic letters (2021)
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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