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Dearomatizing annelation of five-membered rings to naphthalenes by organolithium cyclization.

Authors
  • Clayden, Jonathan
  • Kenworthy, Martin N
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Mar 07, 2002
Volume
4
Issue
5
Pages
787–790
Identifiers
PMID: 11869128
Source
Medline
License
Unknown

Abstract

[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.

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