Chiral Ionic Phosphites and Diamidophosphites: A Novel Group of Efficient Ligands for Asymmetric Catalysis

Gavrilov, K. N.; Lyubimov, S. E.; Bondarev, Oleg G.; Maksimova, M. G.; Zheglov, Sergey V.; Petrovskii, P. V.; Davankov, V. A.; Reetz, Manfred T.

doi:10.1002/adsc.200600372

Cited by 47 publications

(10 citation statements)

References 56 publications

(29 reference statements)

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“…The palladium-catalyzed allylic substitution has also been used as a benchmark reaction for testing a variety of phosphorusbased monodentate ligands (see below and Ref. [331][332][333][334]).…”

Section: Palladium-catalyzed Allylic Substitution Reactionsmentioning

confidence: 99%

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Teichert¹,

Feringa²

2010

Angew Chem Int Ed

648

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: Palladium-catalyzed Allylic Substitution Reactionsmentioning

confidence: 99%

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Teichert¹,

Feringa²

2010

Angew Chem Int Ed

648

340

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“…Zudem diente die Pd-katalysierte allylische Substitution als Testreaktion zur Untersuchung verschiedener einzähniger Phosphorliganden (siehe unten und Liz. [331][332][333][334] [336,337] allerdings konnten keine wesentlichen Verbesserungen der zuvor beschriebenen Methode erreicht werden. Die Pd-katalysierten allylischen Substitutionen von Cyclohexenyl-und Cyclopentenylacetat mit verschiedenen Binaphthyl-und Biphenol-PhosphoramiditLiganden L2 und L16 (siehe Abbildungen 4 und 5) verliefen mit nur schlechten Enantioselektivitäten.…”

Section: Palladiumkatalysierte Allylische Substitutionenunclassified

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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“…31 Monodentate ferrocene-based P ligands L87 and L88 used in AAA 130 L. Milhau and P.J. Guiry L92 was used in allylic sulfonylation with p-TolSO 2 Na [128]. In the presence of BF 4 À as counterion, an exceptional ee of 99% was obtained (Scheme 24).…”

Section: L87 L88mentioning

confidence: 97%

“…32). Gavrilov developed ligands L93-L95 [126,128,129], while Lyubimov worked on L96 [130]. When the oxygen side chain was not chiral, formation of the S product was favored in AAA.…”

Section: L87 L88mentioning

confidence: 98%

Palladium-Catalyzed Enantioselective Allylic Substitution

Milhau

Guiry

2011

Topics in Organometallic Chemistry

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Palladium-catalyzed allylic substitution is one of the main reactions for testing new chiral ligands. The most relevant examples from the work published in the period 2007 to mid-2010 are reviewed. The vast majority of the work published within this timeframe relies upon the application of chiral ligands for asymmetric induction. The recent advances in the development and applications of new chiral P-P, P-N, P-O, P-S, N-N, N-S, S-S, and NHC ligands are covered and are the main focus of this chapter. Other aspects of enantioselective palladium allylic alkylations are discussed in the subsequent sections, for example, heterogeneous catalysis, the use of chiral salt additives, and recent applications in kinetic resolution.

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Chiral Ionic Phosphites and Diamidophosphites: A Novel Group of Efficient Ligands for Asymmetric Catalysis

Cited by 47 publications

References 56 publications

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Phosphoramidite: privilegierte Liganden in der asymmetrischen Katalyse

Palladium-Catalyzed Enantioselective Allylic Substitution

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