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Development of a [3+3] Cycloaddition Strategy toward Functionalized Piperidines

Hedley, Simon J., Moran, Wesley J., Price, David A. and Harrity, Joseph P. A. (2003) Development of a [3+3] Cycloaddition Strategy toward Functionalized Piperidines. The Journal of Organic Chemistry, 68 (11). pp. 4286-4292. ISSN 00223263

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Abstract

This paper describes a novel route to functionalized piperidines via a formal [3+3] cycloaddition reaction of activated aziridines and palladium−trimethylenemethane (Pd-TMM) complexes. The cycloaddition reaction generally proceeds enantiospecifically with ring opening at the least hindered site of the aziridine. Therefore, readily available enantiomerically pure 2-substituted aziridines can be utilized to prepare enantiomerically pure 2-substituted piperidines in good to excellent yield. The N-substituent on the aziridine proved to be crucial to the success of this reaction with only 4-toluenesulfonyl (Ts) and 4-methoxybenzenesulfonyl (PMBS) aziridines permitting smooth cycloaddition to take place. Additionally, spirocyclic aziridines have been found to participate in the [3+3] cycloaddition reaction, whereas 2,3-disubstituted aziridines can be applied to provide fused bicyclic piperidines, albeit in low yield.

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
School of Applied Sciences > Biomolecular Sciences Research Centre
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Depositing User: Graham Stone
Date Deposited: 24 Apr 2009 11:34
Last Modified: 02 Jun 2009 13:40
URI: http://eprints.hud.ac.uk/id/eprint/4037

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