Bromoporphyrins as versatile synthons for modular construction of chiral porphyrins: Cobalt-catalyzed highly enantioselective and diastereoselective cyclopropanation

Ying Chen, Kimberly B. Fields, X. Peter Zhang

Research output: Contribution to journalArticle

Abstract

5,10-Bis(2′,6′-dibromophenyl)porphyrins bearing various substituents at the 10 and 20 positions were demonstrated to be versatile synthons for modular construction of chiral porphyrins via palladium-catalyzed amidation reactions with chiral amides. The quadruple carbon-nitrogen bond formation reactions were accomplished in high yields with different chiral amide building blocks under mild conditions, forming a family of D2-symmetric chiral porphyrins. Cobalt(II) complexes of these chiral porphyrins were prepared in high yields and shown to be active catalysts for highly enantioselective and diastereoselective cyclopropanation under a practical one-pot protocol (alkenes as limiting reagents and no slow addition of diazo reagents).

Original languageEnglish (US)
Pages (from-to)14718-14719
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number45
DOIs
StatePublished - Nov 17 2004

ASJC Scopus subject areas

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

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