Dearomatizing annelation of five-membered rings to naphthalenes by organolithium cyclization.
[reaction: see text] gamma-Lithiopropylnaphthalenes and their oxa- and aza-tethered analogues cyclize by nucleophilic addition of the organolithium to the naphthalene ring. The resulting benzyllithiums react stereoselectively with electrophiles to give dearomatized tricyclic products with structural similarity to the arylnaphthalene lignans.
Clayden
Jonathan
J
Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK. j.p.clayden@man.ac.uk
Kenworthy
Martin N
MN