Formation of All-Carbon Quaternary Centers by Copper-Catalyzed Asymmetric Conjugate Addition

Alexakis, Alexandre; Vuagnoux‐d'Augustin, Magali; Martín, David; Kehrli, Stefan; Palais, Laetitia; Henon, Hélène; Hawner, Christine

doi:10.2533/chimia.2008.461

Cited by 17 publications

(5 citation statements)

References 25 publications

(30 reference statements)

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“…This method could be extended to cyclopentenones. [228] The abovementioned additions of trialkyl aluminum reagents are valuable methods for the generation of chiral all-carbon-quaternary centers, [229] including those with aryl substituents (Scheme 39). [230] The copper-catalyzed conjugate addition to 3-methylcyclohexenone (116) could successfully be carried out in the presence of phosphoramidite L25 by employing in situ prepared diethyl-aryl-alane reagents 117 (compare Scheme 38).…”

Section: Copper-catalyzed Conjugate Additions With Trialkyl Aluminum mentioning

confidence: 99%

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Teichert¹,

Feringa²

2010

Angew Chem Int Ed

638

340

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Asymmetric catalysis with transition-metal complexes is the basis for a vast array of stereoselective transformations and has changed the face of modern synthetic chemistry. Key to this success has been the design of chiral ligands to control the regio-, diastereo-, and enantioselectivity. Phosphoramidites have emerged as a highly versatile and readily accessible class of chiral ligands. Their modular structure enables the formation of ligand libraries and easy fine-tuning for a specific catalytic reaction. Phosphoramidites frequently show exceptional levels of stereocontrol, and their monodentate nature is essential in combinatorial catalysis, where a ligand-mixture approach is used. In this Review, recent developments in asymmetric catalysis with phosphoramidites used as ligands are discussed, with a focus on the formation of carbon-carbon and carbon-heteroatom bonds.

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Section: Copper-catalyzed Conjugate Additions With Trialkyl Aluminum mentioning

confidence: 99%

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Teichert¹,

Feringa²

2010

Angew Chem Int Ed

638

340

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“…Diese Methode wurde auch auf Cyclopentenone angewendet. [228] Die genannten Additionen von Trialkylaluminiumreagentien sind wertvolle Methoden zum Aufbau von chiralen quartären all-Kohlenstoffzentren, [229] darunter auch solchen mit Arylsubstituenten (Schema 39). [230] …”

Section: Kupferkatalysierte Konjugierte Additionen Mit Trialkylaluminunclassified

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

2010

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Die asymmetrische Katalyse mit Übergangsmetallkomplexen ist die Grundlage unzähliger stereoselektiver Umwandlungen und hat damit das Bild der modernen Synthesechemie gewandelt. Der Schlüssel zum Erfolg war die Entwicklung chiraler Liganden zur Kontrolle der Regio‐, Diastereo‐ und Enantioselektivität. Dabei haben sich Phosphoramidite als eine äußerst vielseitige und leicht zugängliche Klasse von chiralen Liganden erwiesen. Ihre modulare Struktur ermöglicht die Herstellung von Ligandenbibliotheken und erleichtert die Feinabstimmung für eine bestimmte katalytische Reaktion. Phosphoramidite bewirken oft außerordentlich hohe Stereoselektivitäten, und ihre einzähnige Natur ist in der kombinatorischen Katalyse, die gemischte Liganden verwendet, unverzichtbar. In diesem Aufsatz werden neue Entwicklungen in der asymmetrischen Katalyse mit Phosphoramiditen diskutiert, wobei der Schwerpunkt auf der Bildung von Kohlenstoff‐ Kohlenstoff‐ und Kohlenstoff‐Heteroatom‐Bindungen liegt.

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“…In this context, the asymmetric conjugate addition represents a powerful tool for the elaboration of these particular stereocenters. Despite well-established transition-metal-based catalytic methods, the generation of all-carbon quaternary stereocenters via Michael addition still constitutes a formidable challenge owing to additional steric hindrance considerations . In the past decade, extensive studies have been devoted to the development of organocatalytic systems performing with excellent enantioselectivities, employing simple substrates.…”

mentioning

confidence: 99%

A Cooperative Participation of the Amido Group in the Organocatalytic Construction of All-Carbon Quaternary Stereocenters by Michael Addition with β-Ketoamides

et al. 2011

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The secondary amido group of α-substituted β-ketoamides plays a crucial role in the control of the reactivity and spatial arrangement (selectivity) in the organocatalyzed Michael addition to unsaturated carbonyls. This results in an unprecedented activation mode of substrates through H-bonding interactions allowing the construction of enantiomerically enriched functionalized all-carbon quaternary centers and spiroaminals of high synthetic potential.

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Formation of All-Carbon Quaternary Centers by Copper-Catalyzed Asymmetric Conjugate Addition

Cited by 17 publications

References 25 publications

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

A Cooperative Participation of the Amido Group in the Organocatalytic Construction of All-Carbon Quaternary Stereocenters by Michael Addition with β-Ketoamides

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