The ‘Mikami’-Catalyst in Enantioselective Diels–Alder Reactions of Juglone-Based Dienophiles with Different 1-Oxygenated Dienes: An Investigation on the Substitution Pattern Dependent Regioselectivity

Dietrich Böse; Wolfgang Frey; Jörg Pietruszka

doi:10.1055/s-0034-1378230

Synthesis, Table of Contents

Synthesis 2014; 46(18): 2524-2532
DOI: 10.1055/s-0034-1378230

paper

The ‘Mikami’-Catalyst in Enantioselective Diels–Alder Reactions of Juglone-Based Dienophiles with Different 1-Oxygenated Dienes: An Investigation on the Substitution Pattern Dependent Regioselectivity

Dietrich Böse

^aInstitut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, 52426 Jülich, Germany

,

Wolfgang Frey

^bInstitut für Organische Chemie, Universität Stuttgart, 70569 Stuttgart, Germany

,

Jörg Pietruszka*

^aInstitut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, 52426 Jülich, Germany

^cInstitut für Bio- und Geowissenschaften (IBG-1: Biotechnologie), Forschungszentrum Jülich, 52428 Jülich, Germany Fax: +49(2461)611669 Email: j.pietruszka@fz-juelich.de

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Abstract

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Abstract

A mechanistic study investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed Diels–Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity.

Key words

catalysis - Diels–Alder reaction - Lewis acids - regioselectivity - enantioselectivity

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References

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