Construction of Azacycles by Intramolecular Amination of Organoboronates and Organobis(boronates)
Peilin Xu, Mingkai Zhang, Bryan T. Ingoglia, Christophe Allais, Anne‐Marie Dechert‐Schmitt, Robert A. Singer, James P. Morken
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.
Topics & Concepts
AminationChemistryIntramolecular forceStereospecificityReductive aminationCombinatorial chemistryStereochemistryOrganic chemistryCatalysisOrganoboron and organosilicon chemistryChemical Synthesis and AnalysisSynthesis and Catalytic Reactions