Palladium-mediated synthesis of novel meso-chiral porphyrins: Cobalt-catalyzed cyclopropanation

Ying Chen, Guang Yao Gao, X. Peter Zhang

Research output: Contribution to journalArticlepeer-review

Abstract

A series of novel meso-chiral porphyrins were effectively synthesized from reactions of 5,15-dibromo-10,20-diarylporphyrins with readily available chiral alcohols and amides via palladium-mediated C-N and C-O bond formations. Cobalt complexes of these chiral porphyrins were prepared and shown to be effective catalysts for cyclopropanation of styrene with ethyl diazoacetate under mild and practical conditions, affording the desired cyclopropane ester as a trans-dominant form in excellent yields. Due to orientation and flexibility of the chiral appendages, only low enantioselectivity was observed.

Original languageEnglish (US)
Pages (from-to)4965-4969
Number of pages5
JournalTetrahedron Letters
Volume46
Issue number30
DOIs
StatePublished - Jul 25 2005

Keywords

  • C-N bond formation
  • C-O bond formation
  • Chiral porphyrins
  • Cobalt porphyrins
  • Cross-coupling
  • Cyclopropanation
  • Palladium-catalyzed

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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