2.7 Metal-Catalyzed (4 + 3) Cycloadditions Involving Allylic Cations

D. E. Jones; M. Harmata

doi:10.1055/sos-SD-222-00176

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Gao, S. et al.: 2016 Science of Synthesis, 2016/4b: Metal-Catalyzed Cyclization Reactions 2 DOI: 10.1055/sos-SD-222-00176

Metal-Catalyzed Cyclization Reactions 2

2.7 Metal-Catalyzed (4 + 3) Cycloadditions Involving Allylic Cations

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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

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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 (4 + 3)-cycloaddition reaction is a reaction between an allylic cation and diene. It is a powerful process and one of the few reactions that directly generates seven-membered ring systems. This reaction exhibits high levels of diastereoselectivity and regioselectivity, which makes it attractive for the rapid construction of complex targets. Several select, reliable, and reproducible methods for the generation and capture of allylic cations by 1,3-dienes using metal catalysis or mediation are presented in this review along with some representative examples of the use of (4 + 3) cycloadditions in the synthesis of natural products.

Key words

(4 + 3) cycloaddition - intramolecular - intermolecular - allylic cations - oxyallylic cations - chiral cations - 1,3-dienes - regioselective - diastereoselective - stereoselective - asymmetric - enantioselective - metal-catalyzed - metal-mediated

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