Enantioselective Diels-Alder reactions

Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts

James M Takacs, Edward C. Lawson, Michael J. Reno, Mark A. Youngman, David A. Quincy

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

A series of chiral bis(oxazoline) ligands, differing in the length of the chain connecting the chiral oxazoline subunits and in the nature of the substituent at the chiral center, were examined in the room temperature Zn(OTf)2, Mg(OTf)2 and Cu(OTf)2 catalyzed reaction of N-crotonyloxazolidinone with cyclopentadiene. A 1,4-bis(oxazoline) ligand proved best for Zn(OTf)2 and afforded product consistent with reaction via an octahedral model, while 1,3-bis(oxazoline) ligands were best for Mg(OTf)2 and Cu(OTf)2.

Original languageEnglish (US)
Pages (from-to)3073-3078
Number of pages6
JournalTetrahedron Asymmetry
Volume8
Issue number18
DOIs
StatePublished - Sep 25 1997

Fingerprint

Diels-Alder reactions
Cycloaddition Reaction
Magnesium
magnesium
Zinc
Copper
zinc
Ligands
catalysts
copper
ligands
Catalysts
Temperature
room temperature
Cyclopentanes
products
trifluoromethanesulfonic acid

ASJC Scopus subject areas

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

Cite this

Enantioselective Diels-Alder reactions : Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts. / Takacs, James M; Lawson, Edward C.; Reno, Michael J.; Youngman, Mark A.; Quincy, David A.

In: Tetrahedron Asymmetry, Vol. 8, No. 18, 25.09.1997, p. 3073-3078.

Research output: Contribution to journalArticle

Takacs, James M ; Lawson, Edward C. ; Reno, Michael J. ; Youngman, Mark A. ; Quincy, David A. / Enantioselective Diels-Alder reactions : Room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts. In: Tetrahedron Asymmetry. 1997 ; Vol. 8, No. 18. pp. 3073-3078.
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