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Gao, S. et al.: 2016 Science of Synthesis, 2016/4b: Metal-Catalyzed Cyclization Reactions 2 DOI: 10.1055/sos-SD-222-00100
Metal-Catalyzed Cyclization Reactions 2

2.4 1,3-Dipolar Cycloadditions Involving Carbonyl or Azomethine Ylides

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Book

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

Carbonyl ylides, which behave as active 1,3-dipole species, have found numerous applications in organic synthesis, especially in the formation of five-membered heterocycles. Among the versatile transformations of carbonyl ylides, 1,3-dipolar cycloadditions with π-bonds, including (3 + 2)-cycloaddition reactions with carbon–carbon π-bonds, aldehydes, and imines, are ubiquitous and important reactions. This chapter focuses on recent advances in these catalytic (3 + 2)-cycloaddition reactions and the examples presented emphasize the chemo-, diastereo-, and enantiocontrol that can be achieved. Also described are selected examples of cycloaddition reactions with azomethine ylides, which behave with similar reactivity to carbonyl ylides, to give the corresponding N-heterocycles. In addition, some selected applications of these (3 + 2)-cycloaddition reactions in natural product synthesis are highlighted.

Key words

(3 + 2) cycloaddition - carbonyl ylides - azomethine ylides - 1,3-dipoles - diazo compounds - chiral dirhodium carboxylates - heterocycles - five-membered rings - natural product synthesis - asymmetric catalysis
 
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