2.3 Pauson–Khand Reactions

G. Dominguez; J. Pérez Castells

doi:10.1055/sos-SD-222-00068

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Gao, S. et al.: 2016 Science of Synthesis, 2016/4b: Metal-Catalyzed Cyclization Reactions 2 DOI: 10.1055/sos-SD-222-00068

Metal-Catalyzed Cyclization Reactions 2

2.3 Pauson–Khand Reactions

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Editors: Gao, S.; Ma, S.

Authors: Bora, U.; Dominguez, G.; Du, H.; Garve, L.; Harmata, M.; Hu, W.; Jones, D. E.; Lee, D.; Li, X.; Mondal, M.; Pérez Castells, J.; Sabbasani, V. R.; Shibata, Y.; Tanaka, K.; Tang, W.; Werz, D. B.; Xia, F.; Xu, X.; Ye, S.

Title: Metal-Catalyzed Cyclization Reactions 2

Print ISBN: 9783131998118; Online ISBN: 9783132404823; Book DOI: 10.1055/b-004-129734

1st edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

The Pauson–Khand (2 + 2 + 1) cycloaddition (PKR) is one of the best ways to construct a cyclopentenone. In this review, standard procedures to perform both stoichiometric and catalytic Pauson–Khand reactions are presented. These include the use of homo- and heterogeneous catalysts as well as different promoters. Asymmetric versions are described, as are cascade processes where the Pauson–Khand reaction is combined with other transformations. The chapter ends with a summary of representative total syntheses of natural products where a Pauson–Khand reaction is used as the key step.

Key words

Pauson–Khand - cycloaddition - transition-metal catalysis - stereoselectivity - asymmetric synthesis - cobalt - rhodium - iridium - heterogeneous catalysis - cascade synthesis - total synthesis

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