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Snyder, S. A.: 2016 Science of Synthesis, 2015/4b: Applications of Domino Transformations in Organic Synthesis 2 DOI: 10.1055/sos-SD-220-00038
Applications of Domino Transformations in Organic Synthesis 2

2.1.2 Domino Reactions Including [2 + 2], [3 + 2], or [5 + 2] Cycloadditions

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Buch

Herausgeber: Snyder, S. A.

Autoren: Bella, M.; Blond, G.; Boyce, J.; Coldham, I.; Dömling, A.; Donnard, M.; Guerrero, C. A.; Gulea, M.; Kroon, E.; Moliterno, M.; Neochoritis, C. G.; Novikov, A. V.; Porco Jr., J. A.; Renzi, P.; Salvio, R.; Schaumann, E.; Sheikh, N. S.; Song, A.; Sorensen, E. J.; Suffert, J.; Zarganes Tzitzikas, T.; Wang, W.; West, G. J.; Yeung, Y.-Y.; Yu, Z. W.; Zakarian, A.

Titel: Applications of Domino Transformations in Organic Synthesis 2

Print ISBN: 9783132211414; Online ISBN: 9783132402218; Buch-DOI: 10.1055/b-003-128260

1st edition © 2016. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

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Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

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

Typ: Mehrbändiges Werk

Auch verfügbar auf Science of Synthesis
 


I. Coldham; N. S. Sheikh

Abstract

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This chapter covers examples of domino reactions that include a [2 + 2]-, [3 + 2]-, or [5 + 2]-cycloaddition reaction. The focus is on concerted reactions that occur in a tandem sequence in one pot, rather than overall “formal cycloadditions” or multicomponent couplings. The cycloaddition step typically involves an alkene or alkyne as one of the components in the ring-forming reaction. In addition to the key cycloaddition step, another bond-forming reaction will be involved that can precede or follow the cycloaddition. This other reaction is often an alkylation that generates the substrate for the cycloaddition, or is a ring-opening or rearrangement reaction that occurs after the cycloaddition. As the chemistry involves sequential reactions including at least one ring-forming reaction, unusual molecular structures or compounds that can be difficult to prepare by other means can be obtained. As a result, this strategy has been used for the regio- and stereoselective preparation of a vast array of polycyclic, complex compounds of interest to diverse scientific communities.

Schlüsselwörter

alkylation - [2 + 2] cycloaddition - [3 + 2] cycloaddition - [5 + 2] cycloaddition - dipolar cycloaddition - domino reactions - Nazarov cyclization - ring formation - [3,3]-sigmatropic rearrangement - tandem reactions
 
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