Sign up & Download
Sign in

A diastereoselective radical cyclization approach to substituted quinuclidines

by Thomas A. Hunt, Andrew F. Parsons, Robert Pratt
Journal of Organic Chemistry ()

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 S(N)2-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.

Cite this document (BETA)

Readership Statistics

3 Readers on Mendeley
by Discipline
 
by Academic Status
 
33% Lecturer
 
33% Post Doc
 
33% Researcher (at an Academic Institution)
by Country
 
33% United Kingdom
 
33% United States

Sign up today - FREE

Mendeley saves you time finding and organizing research. Learn more

  • All your research in one place
  • Add and import papers easily
  • Access it anywhere, anytime

Start using Mendeley in seconds!

Already have an account? Sign in