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Synlett 2007(3): 0360-0373  
DOI: 10.1055/s-2007-967959
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Sulfur-Containing Chiral Ferrocene Derivatives: Synthesis and Applications

Bianca F. Bonini*, Mariafrancesca Fochi, Alfredo Ricci*
Dipartimento di Chimica Organica ‘A. Mangini’, Facoltà di Chimica Industriale, Università di Bologna, Viale Risorgimento 4, 40136 Bologna, Italy
Fax: +39(051)2093654; e-Mail: ricci@ms.fci.unibo.it;
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Publication History

Received 13 July 2006
Publication Date:
07 February 2007 (online)

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Abstract

This account describes the different synthetic approaches used for the preparation of sulfur-containing chiral ferrocenes in which a CFc-S bond is present and the strategies for introducing planar and central chirality. The advantages of using these compounds as ligands for soft metals like palladium and copper are highlighted for several catalytic reactions, including the palladium-catalyzed enantioselective allylic alkylation, epoxidation, and aza-Diels-­Alder reactions.

  • 1 Introduction

  • 2 Synthesis of Planar Chiral Ferrocenes Containing Sulfur Functionalities

  • 2.1 Diastereoselective ortho-Lithiation of Ferrocenyl ­Derivatives Bearing Carbon-Based Chiral Auxiliaries

  • 2.2 Planar Chirality by Enantioinduction Using Alkyllithium/
    (-)-Sparteine Reagent

  • 2.3 Diastereoselective ortho-Metalation of Ferrocenyl ­Derivatives Bearing Chiral Sulfur Directing Groups

  • 2.3.1 Diastereoselective ortho-Lithiation of Chiral Ferrocenyl Sulfoxides

  • 2.3.2 Other Chiral Sulfur ortho-Directing Groups

  • 2.3.3 Ortho-Directed Metalation Involving Chiral Phosphorus Auxiliaries

  • 2.4 Chiral Ferrocenyl Sulfoxides as Interchangeable Directing Groups

  • 3 Thio-Substituted Ferrocenyl Derivatives as Ligands in Asymmetric Catalysis

  • 3.1 S,S Ferrocenyl Ligands

  • 3.2 S,P Ferrocenyl Ligands

  • 3.3 S,N Ferrocenyl Ligands

  • 3.4 S,Oxazoline Ferrocenyl Ligands

  • 4 Thioferrocenyl-Based Pincer Ligands

  • 5 Potentially Biologically Active Ferrocenyl Derivatives

  • 5.1 Ferrocene-Containing β-Lactams

  • 6 Conclusions and Outlook

Key words

metallocenes - sulfur - chirality - ligands - asymmetric ­catalysis