2.2.2 [4 + 2] Cycloaddition

L. Voskressensky; A. Festa

doi:10.1055/sos-SD-211-00080

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Müller, T. J. J.: 2014 Science of Synthesis, 2013/6: Multicomponent Reactions, Volume 2 DOI: 10.1055/sos-SD-211-00080

Multicomponent Reactions, Volume 2

2.2.2 [4 + 2] Cycloaddition

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Editor: Müller, T. J. J.

Authors: Alavijeh, N. S.; Arndtsen, B. A.; Balalaie, S.; Bonne, D.; Chen, C.; Coquerel, Y.; Elliott, M.; Festa, A.; Fusano, A.; Ghabraie, E.; Jones, D. H.; Modha, S.; Müller, T. J. J.; Purushothaman, S.; Raghunathan, R.; Rodriguez, J.-A.; Ryu, I.; Sarvary, A.; Shaabani, A.; Shaabani, S.; Szabó, K. J.; Takasu, K.; Tjutrins, J.; Van der Eycken, E.; Voskressensky, L.; Wan, J.; Xi, C.

Title: Multicomponent Reactions, Volume 2

Subtitle: Reactions Involving an α,α-Unsaturated Carbonyl Compound as Electrophilic Component, Cycloadditions, and Boron-, Silicon-, Free-Radical-, and Metal-Mediated Reactions

Print ISBN: 9783131728319; Online ISBN: 9783132064317; Book DOI: 10.1055/b-003-125831

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Multicomponent Reactions

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.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

The Diels–Alder reaction, with its diverse and extremely rich synthetic potential, is a powerful protocol in synthetic strategies toward natural and unnatural carbo- and heterocycles. This chapter describes multicomponent reaction sequences in which a [4 + 2]-cycloaddition reaction is a key step. In contrast to Section 2.1.7, the focus here is on cycloaddition reactions not involving α, β-unsaturated carbonyl compounds. Examples are described both where the [4 + 2] cycloaddition is the first step in the multicomponent sequence and where the [4 + 2] cycloaddition is a later step in the sequence, with the requisite diene and/or dienophile being formed in the initial steps.

Key words

Diels–Alder reaction - cycloaddition - dienes - heterodienes - dienophiles - carbocycles - heterocycles - allylboration - hydrovinylation - Povarov reaction - Knoevenagel reaction

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