The intramolecular Stille reaction

Duncton, Matthew A. J.; Pattenden, Gerald

doi:10.1039/a808261h

Cited by 155 publications

(60 citation statements)

References 67 publications

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“…[75] Today, the Stille reaction constitutes a reliable and often-used method for the construction of carbocyclic and heterocyclic rings, be they common, medium or large. [76] A striking example of this type of reaction is the pioneering stitching-cyclization reaction applied by the Nicolaou group to construct rapamycin (76) from the bis(vinyl iodide) precursor 72 and trans-1,2-distannyl ethylene 73 (Scheme 14 a).…”

Section: The Stille Reactionmentioning

confidence: 99%

Palladium‐Catalyzed Cross‐Coupling Reactions in Total Synthesis

2005

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In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.

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Section: The Stille Reactionmentioning

confidence: 99%

Palladium‐Catalyzed Cross‐Coupling Reactions in Total Synthesis

2005

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“…In fact it has been applied successfully to the construction of a variety of ring systems bearing sensitive functional groups. [12] Notable examples are the syntheses of dynemicin A by Danishefsky and co-workers [13] and rapamycin by Nicolaou and co-workers, [14] in which double couplings are used for the formation of two CÀC bonds are formed in a single step.…”

Section: Palladium-catalyzed Cross-coupling Reactionsmentioning

confidence: 99%

The Mechanisms of the Stille Reaction

2004

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Eighteen years ago in Angewandte Chemie John K. Stille reviewed a novel methodology, which eventually became known by his name, for the coupling of organostannanes with organic electrophiles. Since then that seed has blossomed into a multifaceted methodology full of hidden possibilities to explore, discover, and enjoy. Very recent modifications are making synthetic wishes come true that were only dreamed of a few years ago. Moreover, as important advances are being made in the understanding of the mechanistic details of the process, it is becoming increasingly possible to apply this essential reaction and its new variants in a less empirical way. The purpose of this Review is to give a critical account of this progress.

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“…[75] Heute wird die Stille-Reaktion als zuverlässige Methode häufig zur Konstruktion carbocyclischer und heterocyclischer Ringe angewandt, seien sie nun normal, mittelgroß oder groß. [76] Ein herausragendes Beispiel ist die "vernähende Cyclisierung" bei der Synthese von Rapamycin (76) [78] die über die acyclische Vorstufe 75 verlief (Schema 14 b). [79,80] Eine weitere spektakuläre "vernähende Cyclisierung" durch eine doppelte Stille-Reaktion setzten Danishefsky und Mitarbeiter in der Totalsynthese des antitumoraktiven Endiin-Antibiotikums Dynemicin (81) Der Einsatz von Übergangsmetallen zur Bildung von Aryl-Aryl-Bindungen reicht bis Anfang des 20.…”

Section: Stille-reaktionenunclassified

Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese

2005

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Wenn man die Entwicklung der organischen Chemie betrachtet, kommt man schnell zu dem Schluss, dass kein Reaktionstyp dieses Gebiet in vergleichbarer Weise geprägt hat wie die Kohlenstoff‐Kohlenstoff‐Kupplungen. Grignard‐, Diels‐Alder‐ und Wittig‐Reaktionen sind nur drei herausragende Beispiele für solche Prozesse, die im vergangenen Jahrhundert zweifellos entscheidend am Aufstieg der chemischen Synthese beteiligt waren. Im letzten Viertel des 20. Jahrhunderts bereicherte eine neue Familie von leistungsfähigen Reaktionen zur Knüpfung von Kohlenstoff‐Kohlenstoff‐Bindungen das Repertoire der Synthesechemie: die übergangsmetallkatalysierten Reaktionen, allen voran die palladiumkatalysierten Kreuzkupplungen. In diesem Aufsatz werden Auszüge aus einer Reihe von ausgewählten Synthesen diskutiert. Die Beispiele sollen die enorme Leistungsfähigkeit dieser Prozesse in der Kunst der Totalsynthese aufzeigen und ihr Potenzial für zukünftige chemische Synthesen unterstreichen.

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The intramolecular Stille reaction

Cited by 155 publications

References 67 publications

Palladium‐Catalyzed Cross‐Coupling Reactions in Total Synthesis

Palladium‐Catalyzed Cross‐Coupling Reactions in Total Synthesis

The Mechanisms of the Stille Reaction

Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese

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