Synthesis 2011(23): 3749-3766  
DOI: 10.1055/s-0031-1289296
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

[2.2]Paracyclophane Derivatives: Synthesis and Application in Catalysis

Jan Paradies*Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)60845637; e-Mail: jan.paradies@kit.edu;
Further Information

Publication History

Received 1 September 2011
Publication Date:
19 October 2011 (eFirst)

  Buy Article Permissions and Reprints

Abstract

Advances in the field of [2.2]paracyclophane chemistry are reviewed including syntheses, resolution of enantiomers and application in organic synthesis. Transition-metal catalyzed as well as organocatalytic transformations are presented focusing on the development of [2.2]paracyclophane derived ligands and catalysts.

1 Introduction

2 [2.2]Paracyclophane Syntheses

3 Ligand Design on the Basis of [2.2]Paracyclophane

4 Application in Asymmetric Catalysis

4.1 Addition of Organozinc Reagents to Carbonyl Compounds

4.2 Application of [2.2]Paracyclophane-Derived Phosphines

4.2.1 Hydrogenation Reactions

4.2.2 Transition-Metal-Catalyzed C-C and C-X Bond Formation Employing Planar-Chiral Phosphines

4.2.3 Planar-Chiral Carbenes

4.2.4 [2.2]Paracyclophanes in Organocatalysis

5 Summary

Key words

[2.2]paracyclophane - catalyst - asymmetric synthesis - phosphine - carbine - hydrogen bond - hydrogenation - cross-coupling