Catalytic Asymmetric Epoxidations with Chiral Iron Porphyrins

John Taylor Groves, Richard S. Myers

Research output: Contribution to journalArticle

462 Scopus citations

Abstract

Iron porphyrins have been modified to include optically active functionalities at the meso positions. Asymmetric epoxidations of prochiral olefins with these chiral iron porphyrins and iodosyl compounds have been investigated. Thus, 5α,10β,15α,20β-tetrakis(o-(R)-hydratropamidophenyl)porphyrin (H2T(α,β,α,β-Hyd)PP) and 5α, 10β,15α,20β-tetrakis(o-[(S)-2′-carboxymethyl-1,1 -binaphthyl-2-carboxamido]phenyl)porphynn (H2T(a,p,a,p-Binap)PP) were synthesized by the condensation of optically active acid chlorides with 5α,10β,5α,20β-tetrakis(o-arninophenyl)porphyrin. Subsequent insertion of iron into H2T(a,p,a,p-Hyd)PP and H2T(a,p,a,p-Binap)PP gave FeT(αβαβ-Hyd)PPCl and FeT(a,p,a,p-Binap)PPCl, respectively. Employing FeT(αβ,αβ-Hyd)PPCl and iodosylbenzene, styrene was oxidized to (R)-(+)-styrene oxide in 31% ee. Similarly, FeT(αβ,αβ-Binap)PPCl and iodosylmesitylene gave (/?)-(+)-styrene oxide in 48% ee. Various substituted styrenes and aliphatic olefins were epoxidized with enantiomeric excesses varying between 0% for 1-methylcyclohexene oxide and 51% for p-chlorostyrene oxide.

Original languageEnglish (US)
Pages (from-to)5791-5796
Number of pages6
JournalJournal of the American Chemical Society
Volume105
Issue number18
DOIs
StatePublished - Jan 1 1983
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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