Die Belluš‐Claisen‐Umlagerung

Gonda, Jozef

doi:10.1002/ange.200301718

Cited by 10 publications

(3 citation statements)

References 69 publications

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“…Of all of the classes of sigmatropic rearrangements, [3,3]-rearrangements have been appliedt he most widely to ring expansion reactions to access medium rings and macrocycles, owing, at least in part, to the sheer diversity of known [3,3]-reactions. For example, the Taylor group utilised the zwitterionic Malherbe-Belluš-Claisen [85,86] rearrangement in as uccinct preparation of 9-membered (E)-olefin containing lactones 207 from 2vinyl tetrahydrofurans 204 (Scheme 36). [87,88] Interestingly,upon tin hydride-mediated radical dechlorination, olefin trans-cis isomerisation was observed to afford exclusively the (Z)-isomers, ag eometry that is generally thermodynamically preferred in nine-membered rings.…”

Section: [33]-sigmatropic Rearrangementsmentioning

confidence: 99%

Ring‐Expansion Reactions in the Synthesis of Macrocycles and Medium‐Sized Rings

Donald

Unsworth

2017

Chemistry A European J

231

108

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Functionalised macrocycles and medium-sized rings have applications in a number of scientific fields, ranging from medicinal chemistry and supramolecular chemistry, to catalysis and nanotechnology. However, their value in these areas can be undermined by a simple, but important limitation: large ring systems are very often difficult to make. Traditional end-to-end cyclisation reactions of long linear precursors are typically unpredictable and impractical processes, mainly due to unfavourable enthalpic and entropic factors. Most published methods to make large rings focus on minimising the damage inflicted by performing the difficult cyclisation step; in contrast, ring-expansion reactions enable it to be avoided altogether. In this Review article, it is highlighted how "growing" rings from existing cyclic systems via ring expansion can expedite the efficient, practical and scalable synthesis of macrocycles and medium-sized rings.

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Section: [33]-sigmatropic Rearrangementsmentioning

confidence: 99%

Ring‐Expansion Reactions in the Synthesis of Macrocycles and Medium‐Sized Rings

Donald

Unsworth

2017

Chemistry A European J

231

108

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“…263 , Scheme 59), which undergo facile [3,3] rearrangement, a variant known as the Belluš–Claisen rearrangement. [88] Such duets have been used extensively for the formation of building blocks for natural product heterocycle synthesis, and benefit from exceptional asymmetric induction when enantiopure substrates are used. [89] Although stoichiometric amounts of Lewis acids are typically required, MacMillan and co-workers [90] made a significant advance in showing that asymmetric induction could be externally controlled by the Lewis acid.…”

Section: [33]-sigmatropic Rearrangementsmentioning

confidence: 99%

Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

et al. 2014

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Catalysis and synthesis are intimately linked in modern organic chemistry. The synthesis of complex molecules is an ever evolving area of science. In many regards, the inherent beauty associated with a synthetic sequence can be linked to a certain combination of the creativity with which a sequence is designed and the overall efficiency with which the ultimate process is performed. In synthesis, as in other endeavors, beauty is very much in the eyes of the beholder.[**] It is with this in mind that we will attempt to review an area of synthesis that has fascinated us and that we find extraordinarily beautiful, namely the combination of catalysis and sigmatropic rearrangements in consecutive and cascade sequences.

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“…B. 263 , Schema ), die einfach in einer [3,3]‐Umlagerung reagieren – eine Variante, die als Belluš‐Claisen‐Umlagerung bekannt ist 88. Solche Duette wurden umfassend genutzt, um Bausteine für die Synthese heterocyclischer Naturstoffe bereit zu stellen; bei Verwendung enantiomerenreiner Substrate zeigen sie eine bemerkenswerte asymmetrische Induktion 89.…”

Section: [33]‐sigmatrope Umlagerungenunclassified

Bis hin zu einer Symphonie der Reaktivität: Kaskaden mit Katalysen und sigmatropen Umlagerungen

et al. 2014

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Die Katalyse und die Synthese sind in der modernen organischen Chemie eng miteinander verbunden. Die Synthese komplexer Moleküle ist ein sich ständig weiterentwickelndes Gebiet. In vielerlei Hinsicht kann die inhärente Schönheit einer Synthesesequenz mit einer bestimmten Kombination aus Kreativität, mit der eine Sequenz entworfen wurde, und der Gesamteffizienz, mit der das endgültige Verfahren durchgeführt wird, in Zusammenhang gebracht werden. Ebenso wie bei anderen Unterfangen liegt bei chemischen Synthesen die Schönheit im Auge des Betrachters. In diesem Sinne werden wir versuchen, ein Gebiet der Synthese zu erörtern, das uns fasziniert, und das wir außergewöhnlich schön finden, nämlich die Kombination aus Katalyse und sigmatropen Umlagerungen in konsekutiven Sequenzen und Kaskadenreaktionen.

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Die Belluš‐Claisen‐Umlagerung

Cited by 10 publications

References 69 publications

Ring‐Expansion Reactions in the Synthesis of Macrocycles and Medium‐Sized Rings

Ring‐Expansion Reactions in the Synthesis of Macrocycles and Medium‐Sized Rings

Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements

Bis hin zu einer Symphonie der Reaktivität: Kaskaden mit Katalysen und sigmatropen Umlagerungen

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