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Rhodium-Catalyzed Intramolecular, Anti-Markovnikov Hydroamination. Synthesis of 3-Arylpiperidines

Akihiro Takemiya and John F. Hartwig*

*Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, Email: john.hartwigyale.edu

A. Takemiya, J. F. Hartwig, J. Am. Chem. Soc., 2006, 128, 6042-6043.

DOI: 10.1021/ja058299e (free Supporting Information)


Abstract

An intramolecular anti-Markovnikov hydroamination of 1-(3-aminopropyl)vinylarenes occurred in the presence of [Rh(COD)(DPPB)]BF4 as catalyst to form 3-arylpiperidines in high yield. Reactants with substituents β to the amino group formed 3,5-disubstituted piperidines with high diastereomeric excess, whereas substituents in α and γ gave mostly enamines and isomerized starting materials.

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Key Words

Piperidines


ID: J48-Y2006-2010