Journal article

A diastereoselective radical cyclization approach to substituted quinuclidines

Hunt T, Parsons A, Pratt R ...see all

Journal of Organic Chemistry, vol. 71, issue 9 (2006) pp. 3656-3659

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Abstract

A new, concise, and flexible approach to novel quinuclidines has been developed, which employs a phosphorus hydride mediated radical addn./cyclization reaction in the key step. 3-Allyl-4-[(Z)-4-tert.-butyldiphenylsilyloxy-2-butenyl]-1,3-oxazolidin-2-one reacts with di-Et thiophosphite in an efficient and diastereoselective radical addn./cyclization reaction to give trisubstituted piperidines. These piperidines are subsequently converted into 2,5-disubstituted quinuclidines using SN2-type cyclizations. Finally, the resulting quinuclidines undergo novel Horner-Wadsworth-Emmons-type reactions to give unsatd. quinuclidines (5RS)-I, which have structures similar to that of (-)-quinine. [on SciFinder(R)]

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Authors

  • Thomas A. Hunt

  • Andrew F. Parsons

  • Robert Pratt

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