Enantioselective Diels-Alder reactions

Novel constrained bis(oxazoline) ligand-metal triflate catalysts

James M Takacs, David A. Quincy, William Shay, Brian E. Jones, Charles R. Ross

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

Five chiral 1,4-bis(oxazoline) ligands, each bearing a bicyclic backbone, were prepared and examined in Mg(OTf)2-, Zn(OTf)2, and Cu(OTf)2 catalyzed Diels-Alder reactions. The cycloadditions were carried out at room temperature and afforded enantiomeric excess up to 88%, Surprisingly, a non-C2-symmetric bis(oxazoline) bearing a meso backbone was among the more efficient ligands examined.

Original languageEnglish (US)
Pages (from-to)3079-3087
Number of pages9
JournalTetrahedron Asymmetry
Volume8
Issue number18
DOIs
StatePublished - Sep 25 1997

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Bearings (structural)
Diels-Alder reactions
Cycloaddition Reaction
Metals
Ligands
catalysts
ligands
Catalysts
Cycloaddition
cycloaddition
metals
Temperature
room temperature

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Enantioselective Diels-Alder reactions : Novel constrained bis(oxazoline) ligand-metal triflate catalysts. / Takacs, James M; Quincy, David A.; Shay, William; Jones, Brian E.; Ross, Charles R.

In: Tetrahedron Asymmetry, Vol. 8, No. 18, 25.09.1997, p. 3079-3087.

Research output: Contribution to journalArticle

Takacs, James M ; Quincy, David A. ; Shay, William ; Jones, Brian E. ; Ross, Charles R. / Enantioselective Diels-Alder reactions : Novel constrained bis(oxazoline) ligand-metal triflate catalysts. In: Tetrahedron Asymmetry. 1997 ; Vol. 8, No. 18. pp. 3079-3087.
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