Asymmetric ortholithiation of amides by conformationally mediated chiral memory: An enantioselective route to naphtho- and benzofuranones

Jonathan Clayden*, Christopher C. Stimson, Martine Keenan

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

19 Citations (Scopus)

Abstract

An enantiomerically pure sulfinyl group ortho to an aromatic amide imposes absolute stereochemistry on the conformation of its Ar-CO axis. Sulfoxide-lithium exchange followed by addition to an aldehyde relays the chirality of the amide axis to the new hydroxyl-bearing stereogenic centre with good stereochemical fidelity. Lactonisation of the hydroxyamide gives naphthofuranones and benzofuranones, including the fungal metabolite isoochracein, but with substrate-dependent stereoselectivity.

Original languageEnglish
Pages (from-to)1716-1720
Number of pages5
JournalSYNLETT
Issue number11
Early online date28 Jun 2005
DOIs
Publication statusPublished - 7 Jul 2005

Keywords

  • Amide
  • Benzofuranone
  • Chiral memory
  • Directed metallation
  • Sulfoxide

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