Synthesis of Phenanthrene Derivatives by Intramolecular Cyclization Utilizing the [1,2]-Phospha-Brook Rearrangement Catalyzed by a Brønsted Base

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Abstract

The synthesis of functionalized phenanthrene derivatives was achieved by intramolecular cyclization utilizing the [1,2]-phospha-Brook rearrangement under Brønsted base catalysis. Treatment of biaryl compounds having an α-ketoester moiety and an alkyne moiety at the 2 and 2′ positions, respectively, with diisopropyl phosphite in the presence of a catalytic amount of phosphazene base P2-tBu provides 9,10-disubstituted phenanthrene derivatives in high yields. This reaction involves the generation of an ester enolate through an umpolung process, that is, addition of diisopropyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, the intramolecular addition to an alkyne, and the [3,3] rearrangement of the allylic phosphate moiety in a consecutive fashion.

Original languageEnglish
Pages (from-to)12577-12580
Number of pages4
JournalChemistry - A European Journal
Volume21
Issue number36
DOIs
Publication statusPublished - 2015 Sep 1

Keywords

  • cyclization
  • organocatalysis
  • phenanthrenes
  • phosphazenes
  • rearrangement

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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