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 Scopus citations

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
Publication statusPublished - Sep 25 1997

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ASJC Scopus subject areas

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

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