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Synthesis of 2,4-Disubstituted Piperidines via Radical Cyclization: Unexpected Enhancement in Diastereoselectivity with Tris(trimethylsilyl)silane

Lucile A. Gandon, Alexander G. Russell, Tatyana Güveli, Angela E. Brodwolf, Benson M. Kariuki, Neil Spencer and John S. Snaith*

*School of Chemistry, The University of Birmingham, Edgbaston, Birmingham, B15 2TT, U.K., Email: j.s.snaithbham.ac.uk

L. A. Gandon, A. G. Russel, T. Güveli, A. E. Brodwolf, B. M. Kariuki, N. Spencer, J. S. Snaith, J. Org. Chem., 2006, 71, 5198-5207.

DOI: 10.1021/jo060495w (free Supporting Information)


Abstract

A novel approach to 2,4-disubstituted piperidines involves the radical cyclization of 7-substituted-6-aza-8-bromooct-2-enoates. An enhancement in diastereoselectivity using tris(trimethylsilyl)silane instead of tributyltin hydride is discussed.

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Key Words

Piperidines, TTMSS


ID: J42-Y2006-1960