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A diastereoselective radical cyclization approach to substituted quinuclidines

Hunt, T.A., Parsons, A.F. and Pratt, R. (2006) A diastereoselective radical cyclization approach to substituted quinuclidines. Journal of Organic Chemistry, 71 (9). pp. 3656-3659. ISSN 0022-3263

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Abstract

A new, concise, and flexible approach to novel quinuclidines has been developed, which employs a phosphorus hydride mediated radical addition/cyclization reaction in the key step. 1,7-Diene 5 reacts with diethyl thiophosphite in an efficient and diastereoselective radical addition/cyclization reaction to give trisubstituted piperidines 4ab. Piperidines 4ab are subsequently converted into 2,5-disubstituted quinuclidines using SN2-type cyclizations. Finally, the resulting quinuclidines are shown to undergo novel Horner−Wadsworth−Emmons-type (HWE-type) reactions to give unsaturated quinuclidines 21a and 21b, which have structures similar to that of (−)-quinine 1.

Item Type: Article
Academic Units: The University of York > Chemistry (York)
Depositing User: York RAE Import
Date Deposited: 17 Apr 2009 13:18
Last Modified: 17 Apr 2009 13:18
Published Version: http://dx.doi.org/10.1021/jo060349q
Status: Published
Publisher: American Chemical Society
Identification Number: 10.1021/jo060349q
URI: http://eprints.whiterose.ac.uk/id/eprint/6798

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