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

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 h...

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Veröffentlicht in:Organic letters 2021-05, Vol.23 (9), p.3379-3383
Hauptverfasser: Xu, Peilin, Zhang, Mingkai, Ingoglia, Bryan, Allais, Christophe, Dechert-Schmitt, Anne-Marie R, Singer, Robert A, Morken, James P
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00856