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Synlett 2005(17): 2547-2570  
DOI: 10.1055/s-2005-918922
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Regioselectivity, Stereoselectivity and Catalysis in Intermolecular Pauson-Khand Reactions: Teaching an Old Dog New Tricks

Sabine Laschat*, Armand Becheanu, Thomas Bell, Angelika Baro
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
Fax: +49(711)6854285; e-Mail: sabine.laschat@oc.uni-stuttgart.de;
Further Information

Publication History

Received 18 July 2005
Publication Date:
05 October 2005 (online)

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Abstract

Since its discovery in the early seventies the inter­molecular Pauson-Khand reaction has made considerable progress towards a powerful synthetic method. This account describes the major accomplishments with respect to reactivity, stereoselectivity and catalytic versions, which have been achieved over the last ­decade and summarizes mechanistic information being obtained by theoretical and experimental studies.

  • 1 Introduction

  • 2 Reactivity: Improvement by Additives

  • 3 Regioselectivity: Some Mechanistic Struggles

  • 4 Stereoselectivity

  • 4.1 Chiral Precursors

  • 4.2 Chiral Auxiliaries

  • 4.3 Chiral Cobalt Complexes

  • 4.4 Chiral Amine N-Oxides

  • 5 Catalysis

  • 5.1 Cobalt-Catalyzed Reactions

  • 5.2 Ruthenium-Catalyzed Reactions

  • 5.3 Rhodium-Catalyzed Reactions

  • 5.4 Iridium-Catalyzed Reactions

  • 6 Theoretical Studies and some Mechanistic Curiosities

  • 7 Conclusions

Key words

Pauson-Khand reaction - metal-catalysis - stereoselectivity - theoretical studies