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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Published inOrganic letters Vol. 23; no. 9; pp. 3379 - 3383
Main Authors Xu, Peilin, Zhang, Mingkai, Ingoglia, Bryan, Allais, Christophe, Dechert-Schmitt, Anne-Marie R, Singer, Robert A, Morken, James P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.05.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PYRROLIDINE
PIPERIDINE
AMINES
PYRIDINE
CHIRAL SYNTHESIS
ORGANIC AZIDES
ORGANOBORANES
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Summary: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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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00856