A reinvestigation of asymmetric induction in <i>Diels-Alder</i> reactions to chiral acrylates

Von Oppolzer, Wolfgang; Kurth, Mark; Reichlin, Daniel; Moffatt, Frank Sutor

doi:10.1016/S0040-4039(01)90516-7

Scientific article

Letter

English

A reinvestigation of asymmetric induction in Diels-Alder reactions to chiral acrylates

ContributorsVon Oppolzer, Wolfgang; Kurth, Mark; Reichlin, Daniel; Moffatt, Frank Sutor

Published inTetrahedron letters, vol. 22, no. 27, p. 2545-2548

Publication date1981

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.

Affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang et al. A reinvestigation of asymmetric induction in <i>Diels-Alder</i> reactions to chiral acrylates. In: Tetrahedron letters, 1981, vol. 22, n° 27, p. 2545–2548. doi: 10.1016/S0040-4039(01)90516-7

Article (Published version)

Identifiers

PID : unige:169217
DOI : 10.1016/S0040-4039(01)90516-7

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S0040403901905167

ISSN of the journal0040-4039

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A reinvestigation of asymmetric induction in Diels-Alder reactions to chiral acrylates

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.

Technical informations

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.