A concise summary of experimental facts about the Soai reaction

Gehring, Timo; Busch, M.; Schlageter, Martin; Weingand, Daniel

doi:10.1002/chir.20849

Cited by 78 publications

(39 citation statements)

References 66 publications

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“…Several authors have summarized the principal trends of the Soai reaction (see for example Ref. 38e). In what follows, we emphasize those characteristics that suggest that the Soai reaction can be described as a Frank‐like reaction network taking place in a closed system giving rise to a kinetically controlled absolute asymmetric synthesis.…”

Section: Thermodynamic Scenario For Spontaneous Mirror Symmetry Brmentioning

confidence: 99%

Absolute Asymmetric Synthesis in Enantioselective Autocatalytic Reaction Networks: Theoretical Games, Speculations on Chemical Evolution and Perhaps a Synthetic Option

Ribó

Blanco

Crusats

et al. 2014

Chemistry A European J

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The Soai reaction and the Viedma deracemization of racemic conglomerate crystal mixtures are experimental pieces of evidence of the ability of enantioselective autocatalytic coupled networks to yield absolute asymmetric synthesis. Thermodynamically open systems or systems with non-uniform energy distributions may lead to chiral final states and, in systems able to come into thermodynamic equilibrium with their surroundings, to kinetically controlled absolute asymmetric synthesis. The understanding of network parameters and of the thermodynamic scenarios that may lead to spontaneous mirror symmetry breaking (SMSB) could assist in the development of new methods for asymmetric synthesis and enantioselective polymerizations (e.g., replicators), and to frame reasonable speculations on the origin of biological homochirality.

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Section: Thermodynamic Scenario For Spontaneous Mirror Symmetry Brmentioning

confidence: 99%

Absolute Asymmetric Synthesis in Enantioselective Autocatalytic Reaction Networks: Theoretical Games, Speculations on Chemical Evolution and Perhaps a Synthetic Option

Ribó

Blanco

Crusats

et al. 2014

Chemistry A European J

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“…Substantial reviews in the field of catalysis have been published by Gibson, Paradies and David 6–8. Further investigations, for example, by Noyori and Soai,9,10 showed that catalysis with [2.2]paracyclophane zinc complexes having a nitrogen–oxygen coordination motif is feasible. In recent years, we combined the rigidity of the [2.2]paracyclophane backbone with novel metal coordinating moieties and described the asymmetric conjugate addition (ACA) of diethylzinc to cinnamaldehyde utilizing different [2.2]paracyclophane ligands 11–13.…”

Section: Introductionmentioning

confidence: 99%

Roadmap towards N‐Heterocyclic [2.2]Paracyclophanes and Their Application in Asymmetric Catalysis

et al. 2013

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A novel family of [2.2]paracyclophane derivatives is described. Different substituted pyrazole, triazole and pyrimidine moieties were introduced to the [2.2]paracyclophane scaffold and the products were characterized spectroscopically and by X‐ray structure analysis. These compounds are promising ligands for application in asymmetric catalysis. We show here that one of these ligands can catalyze asymmetric conjugate addition. Furthermore a palladium complex was synthesized by using a hydroxy‐pyrazolyl[2.2]paracyclophane ligand.

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“…[163,[195][196][197][198][199] Obwohl die genauen Einzelheiten weiter erforscht werden, liefert die Arbeit von Blackmond und Brown [191,[200][201][202][203][204][205][206][207][208][209][210] Autokatalyse ponenten erfolgt schnell und reversibel, wobei die Alkylierung des Aldehyds mit Diisopropylzink der geschwindigkeitsbestimmende Schritt ist. [163,[195][196][197][198][199] Obwohl die genauen Einzelheiten weiter erforscht werden, liefert die Arbeit von Blackmond und Brown [191,[200][201][202][203][204][205][206][207][208][209][210] Autokatalyse ponenten erfolgt schnell und reversibel, wobei die Alkylierung des Aldehyds mit Diisopropylzink der geschwindigkeitsbestimmende Schritt ist.…”

Section: Die Soai-reaktionunclassified

Mechanismen der Autokatalyse

Bissette

Fletcher

2013

Angewandte Chemie

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Selbstreplikation ist ein fundamentales Konzept. Die Vorstellung von einer Entität, die in wiederholender Weise mehr von sich selbst erzeugen kann, hat die Phantasie vieler Denker von Neumann bis Vonnegut angeregt. Über die Wissenschaft und Science‐Fiction hinaus hat das Konzept der Autokatalyse auch in die Ökonomie und Sprachtheorie Eingang gefunden – und es hat Ängste wie etwa vor “gray goo” (graue Schmiere) geschürt. Die Autokatalyse ist von zentraler Bedeutung für die Ausbreitung des Lebens und bildet die Grundlage vieler anderer biologischer Prozesse, einschließlich des modernen Konzepts der Evolution. Organismen können als unvollkommene “Selbstreplikatoren” betrachtet werden, die nah verwandte Spezies erzeugen und auf diese Weise Auslese und Evolution ermöglichen. Folglich führt jegliche Betrachtung der Selbstreplikation zu einer der tiefgreifendsten Fragen überhaupt: Was ist Leben? Selbstreplizierende Minimalsysteme wurden mit dem Ziel untersucht, die zugrundeliegenden Prinzipien lebender Systemen zu begreifen, um damit unsere Konzepte der biologischen Fitness und chemischen Stabilität, der Selbstorganisation und Emergenz weiterzuentwickeln und letztendlich herausfinden zu können, wie aus Chemie Biologie werden konnte.

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A concise summary of experimental facts about the Soai reaction

Cited by 78 publications

References 66 publications

Absolute Asymmetric Synthesis in Enantioselective Autocatalytic Reaction Networks: Theoretical Games, Speculations on Chemical Evolution and Perhaps a Synthetic Option

Absolute Asymmetric Synthesis in Enantioselective Autocatalytic Reaction Networks: Theoretical Games, Speculations on Chemical Evolution and Perhaps a Synthetic Option

Roadmap towards N‐Heterocyclic [2.2]Paracyclophanes and Their Application in Asymmetric Catalysis

Mechanismen der Autokatalyse

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