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

Sabine Laschat; Armand Becheanu; Thomas Bell; Angelika Baro

doi:10.1055/s-2005-918922

ACCOUNT

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;

Abstract

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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

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