Synthesis 2013; 45(8): 1016-1028
DOI: 10.1055/s-0032-1316864
feature article
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Rauhut–Currier-Type Cyclizations via Dienamine Activation: Scope and Mechanism

Eugenia Marqués-López*
a  TU Dortmund University, Faculty of Chemistry, Otto-Hahn-Straße 6, 44227 Dortmund, Germany   Fax: +49(231)7555363   Email: mathias.christmann@tu-dortmund.de
b  Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain[1]   Email: mmaamarq@unizar.es
,
Raquel P. Herrera
a  TU Dortmund University, Faculty of Chemistry, Otto-Hahn-Straße 6, 44227 Dortmund, Germany   Fax: +49(231)7555363   Email: mathias.christmann@tu-dortmund.de
b  Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain[1]   Email: mmaamarq@unizar.es
,
Timo Marks
a  TU Dortmund University, Faculty of Chemistry, Otto-Hahn-Straße 6, 44227 Dortmund, Germany   Fax: +49(231)7555363   Email: mathias.christmann@tu-dortmund.de
,
Wiebke C. Jacobs
a  TU Dortmund University, Faculty of Chemistry, Otto-Hahn-Straße 6, 44227 Dortmund, Germany   Fax: +49(231)7555363   Email: mathias.christmann@tu-dortmund.de
,
Mathias Christmann*
a  TU Dortmund University, Faculty of Chemistry, Otto-Hahn-Straße 6, 44227 Dortmund, Germany   Fax: +49(231)7555363   Email: mathias.christmann@tu-dortmund.de
› Author Affiliations
Further Information

Publication History

Received: 05 November 2012

Accepted after revision: 16 February 2013

Publication Date:
13 March 2013 (online)

Abstract

This Feature Article describes our mechanistic studies in organocatalytic Rauhut–Currier-type reactions and some applications in target-oriented synthesis. The developed approach involves the cyclization of two tethered Michael acceptors via dienamine intermediates and leads to highly functionalized cycloalkenes. The utility of these intermediates is further demonstrated by the synthesis of biologically important targets, such as optically active iridoid derivatives.

1 Introduction

2 Organocatalytic Cyclization of Tethered α,β-Unsaturated Carbonyl Compounds; Synthesis of Cyclopentene Derivatives

2.1 Mechanistic Proposal

2.1.1 ESI-HRMS Measurements

2.1.2 NMR Experiments

2.1.3 Complementary Reactivity

2.2 Synthetic Applications

3 Organocatalytic Cyclization of Tethered α,β-Unsaturated Carbonyl Compounds; Synthesis of Cyclohexene Derivatives

4 Conclusions

Supporting Information

 
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