A reinvestigation of asymmetric induction in diels-alder reactions to chiral acrylates.

Wolfgang Oppolzer, Mark Kurth, Daniel Reichlin, Frank Moffatt

Research output: Contribution to journalArticle

75 Citations (Scopus)

Abstract

The chiral induction in the Diels-Alder addition 1 → 2, assessed reliably by 19F-NMR-spectroscopy of the endo-esters 4, varied between 47 - 93% in favor of the 2-(R)-adducts 2 depending on the auxiliary chiral group and the Lewis-acid catalyst.

Original languageEnglish (US)
Pages (from-to)2545-2548
Number of pages4
JournalTetrahedron Letters
Volume22
Issue number27
DOIs
StatePublished - 1981
Externally publishedYes

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Acrylates
Lewis Acids
Cycloaddition Reaction
Nuclear magnetic resonance spectroscopy
Esters
Magnetic Resonance Spectroscopy
Catalysts

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A reinvestigation of asymmetric induction in diels-alder reactions to chiral acrylates. / Oppolzer, Wolfgang; Kurth, Mark; Reichlin, Daniel; Moffatt, Frank.

In: Tetrahedron Letters, Vol. 22, No. 27, 1981, p. 2545-2548.

Research output: Contribution to journalArticle

Oppolzer, Wolfgang ; Kurth, Mark ; Reichlin, Daniel ; Moffatt, Frank. / A reinvestigation of asymmetric induction in diels-alder reactions to chiral acrylates. In: Tetrahedron Letters. 1981 ; Vol. 22, No. 27. pp. 2545-2548.
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