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Synthesis 2006(4): 687-691  
DOI: 10.1055/s-2006-926306
PAPER
© Georg Thieme Verlag Stuttgart · New York

Quick Access to Optically Pure 2-(1-Hydroxybenzyl)piperidine and Pyrrolidine

José Luis García Ruano*, José Alemán, M. Belén Cid
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain
Fax: +34(914)973966; e-Mail: joseluis.garcia.ruano@uam.es;
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Publication History

Received 28 July 2005
Publication Date:
19 January 2006 (online)

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Abstract

Optically pure 2-(1-hydroxybenzyl)piperidine and pyrrolidine were prepared by reaction of oxygenated 2-(p-tolylsulfinyl)benzyl carbanions with the appropriate chlorinated N-sulfinylimines followed by subsequent elimination of the sulfinyl groups. The main reaction is a tandem process involving nucleophilic addition of the sulfinylbenzyl carbanion to the C=N bond followed by intramolecular elimination of the chlorine by the resulting amide. The matched pair of the reagents (exhibiting the same configuration at their respective sulfinyl moieties) evolves with a complete control of the stereoselectivity at the two newly created chiral carbons.

Key words

piperidines - pyrrolidines - benzyl carbanion - N-sulfinylimines - tandem AN/SNi reaction

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The aldehydes were unstable on silica gel, however, the corresponding N-sulfinylimines were stable under chromatographic conditions.

20

Compounds with these configurations had been shown to be the consonant pair in other previously studied reactions (see reference 16).

21

The authors have deposited atomic coordinates for 7 at the Cambridge Crystallographic Data Centre (deposition number CCDC 277170). The coordinates can be obtained on request from the Director Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.