Synthesis 2014; 46(18): 2524-2532
DOI: 10.1055/s-0034-1378230
paper
© Georg Thieme Verlag Stuttgart · New York

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
a   Institut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, 52426 Jülich, Germany
,
Wolfgang Frey
b   Institut für Organische Chemie, Universität Stuttgart, 70569 Stuttgart, Germany
,
Jörg Pietruszka*
a   Institut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, 52426 Jülich, Germany
c   Institut für Bio- und Geowissenschaften (IBG-1: Biotechnologie), Forschungszentrum Jülich, 52428 Jülich, Germany   Fax: +49(2461)611669   Email: j.pietruszka@fz-juelich.de
› Author Affiliations
Further Information

Publication History

Received: 09 April 2014

Accepted after revision: 06 May 2014

Publication Date:
25 June 2014 (online)


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.

Supporting Information

 
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