Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan

Daisuke Uraguchi, Keiichi Sorimachi, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

328 Citations (Scopus)

Abstract

A new asymmetric entry of the 1,2-aza-Friedel-Crafts reaction catalyzed by a chiral phosphoric acid is described. The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral γ-butenolid.

Original languageEnglish
Pages (from-to)11804-11805
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number38
DOIs
Publication statusPublished - 2004 Sep 29

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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