2.4 1,3-Dipolar Cycloadditions Involving Carbonyl or Azomethine Ylides
Buch
Herausgeber: Gao, S.; Ma, S.
Titel: Metal-Catalyzed Cyclization Reactions 2
Print ISBN: 9783131998118; Online ISBN: 9783132404823; Buch-DOI: 10.1055/b-004-129734
1st edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart
Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
Science of Synthesis Reference Libraries
Übergeordnete Publikation
Titel: Science of Synthesis
DOI: 10.1055/b-00000101
Reihenherausgeber: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Typ: Mehrbändiges Werk
Abstract
![](https://www.thieme-connect.de/media/10.1055-b-004-129734/thumbnails/a_212mcm.jpg)
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.
Schlüsselwörter
(3 + 2) cycloaddition - carbonyl ylides - azomethine ylides - 1,3-dipoles - diazo compounds - chiral dirhodium carboxylates - heterocycles - five-membered rings - natural product synthesis - asymmetric catalysis- 3 Wang J, In Comprehensive Organometallic Chemistry III Crabtree RH, Mingos DMP. Elsevier Oxford 2007; Vol 11 159–163
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