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
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.
|Institution:||The University of York|
|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|
|Publisher:||American Chemical Society|