Issue 16, 2004

Tris(trimethylsilyl)silane: an unprecedented enhancement in the diastereoselectivity of radical cyclisations to give 2,4-disubstituted piperidines

Abstract

Cyclisation of bromides 4af mediated by tributyltin hydride affords predominantly the trans piperidines 5af with modest diastereomeric ratios, while cyclisation with tris(trimethylsilyl)silane affords the same products with diastereomeric ratios of up to 99 : 1.

Graphical abstract: Tris(trimethylsilyl)silane: an unprecedented enhancement in the diastereoselectivity of radical cyclisations to give 2,4-disubstituted piperidines

Article information

Article type
Communication
Submitted
28 Jun 2004
Accepted
02 Jul 2004
First published
16 Jul 2004

Org. Biomol. Chem., 2004,2, 2270-2271

Tris(trimethylsilyl)silane: an unprecedented enhancement in the diastereoselectivity of radical cyclisations to give 2,4-disubstituted piperidines

L. A. Gandon, A. G. Russell and J. S. Snaith, Org. Biomol. Chem., 2004, 2, 2270 DOI: 10.1039/B409714A

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