Threitol-Strapped Manganese Porphyrins as Enantioselective Epoxidation Catalysts of Unfunctionalized Olefins

James P. Collman*, Virgil J. Lee, Cynthia J. Kellen-Yuen, Xumu Zhang, James A. Ibers, John I. Brauman

*Corresponding author for this work

Research output: Contribution to journalArticle

157 Scopus citations

Abstract

Nine members of a family of new chiral porphyrins have been prepared from reactions between ditosylthreitol derivatives and 5,10,15,20-tetrakis(2-hydroxyphenyl)porphyrin. The assignment of the resultant isomers has been made from their 1H NMR spectra and on the basis of an absolute configuration determination from the crystal structure of 4. The chiral frameworks of these systems are easily varied by condensing different aldehydes and ketones with the 2,3-diol of the threitol unit. The manganese derivatives of six of these systems were studied as asymmetric catalysts in the epoxidation of unfunctionalized olefins. Up to 88% ee is obtained in the epoxidation of 1,2-dihydronaphthalene with one of these derivatives, 9, when a bulky imidazole ligand is used to block the unhindered face of the porphyrin catalyst.

Original languageEnglish (US)
Pages (from-to)692-703
Number of pages12
JournalJournal of the American Chemical Society
Volume117
Issue number2
DOIs
StatePublished - Jan 1995

ASJC Scopus subject areas

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

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