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Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization

Ragoussi, Maria-Eleni, Walker, Stephen M., Piccanello, Andrea, Kariuki, Benson, Horton, Peter N., Spencer, Neil and Snaith, John S. 2010. Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization. Journal of Organic Chemistry 75 (21) , pp. 7347-7357. 10.1021/jo101631y

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Abstract

A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto α,β-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2 to 40:1 when the radical stabilizing group is vinyl or phenyl. Cyclization of a (triethylsilyl)vinyl-stabilized radical gives the corresponding piperidine radical as a single diastereoisomer that may either be trapped by tributyltin hydride to afford the 2,4,5-trisubstituted piperidine or undergo a second 5-endo cyclization onto the (triethylsilyl)vinyl substituent to produce the 3,5,7-trisubstituted octahydro2pyrindene as a single diastereoisomer.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Last Modified: 04 Jun 2017 03:31
URI: http://orca-mwe.cf.ac.uk/id/eprint/22398

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