Chiral P*-monodentate phosphite ligand for Pd-catalysed asymmetric allylation reactions

Gavrilov, K. N.; Tsarev, V. N.; Lyubimov, S. E.; Shyryaev, Alexei A.; Zheglov, Sergey V.; Bondarev, Oleg G.; Davankov, V. A.; Kabro, Anzhelika; Moiseev, S. K.; Калинин, В. Н.

doi:10.1070/mc2003v013n03abeh001745

Mendeleev Communications

2003

DOI: 10.1070/mc2003v013n03abeh001745

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Chiral P*-monodentate phosphite ligand for Pd-catalysed asymmetric allylation reactions

K. N. Gavrilov

V. N. Tsarev

S. E. Lyubimov

et al.

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Cited by 6 publications

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“…[46] 1,3-Diphenylallyl acetate 10, methyl (2-phenyl-ortho-carboran-1-yl)phenyl acetate 12 and methyl prop-2-en-1-yl carbonate were prepared by the methods described earlier. [40,44,47] Sodium p-toluenesulfinate (Acros Organics) was dried in vacuo (2 h, 80°C, 1 Torr).…”

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P‐Chiral Monodentate Diamidophosphites − New and Efficient Ligands for Palladium‐Catalysed Asymmetric Allylic Substitution

et al. 2004

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confidence: 99%

P‐Chiral Monodentate Diamidophosphites − New and Efficient Ligands for Palladium‐Catalysed Asymmetric Allylic Substitution

et al. 2004

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Chiral P*‐Monodentate Phosphite Ligand for Pd‐Catalyzed Asymmetric Allylation Reactions.

et al. 2003

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Sulfones Sulfones Q 0600Chiral P*-Monodentate Phosphite Ligand for Pd-Catalyzed Asymmetric Allylation Reactions. -A novel monodentate phosphite ligand with stereogenic phosphorous and carbon atoms, which is easily available from (S)-2-phenylaminomethyl pyrrolidine, is an effective chiral catalyst for the asymmetric allylation of propenyl acetate (I). -(GAVRILOV, K. N.; TSAREV*, V. N.; LYUBIMOV, S. E.; SHYRYAEV, A. A.; ZHEGLOV, S. V.; BONDAREV, O. G.; DAVANKOV, V. A.; KABRO, A. A.; MOISEEV, S. K.; KALININ, V. N.; Mendeleev Commun. 2003, 3, 134-136; Nesmeyanov Inst. Organoelem. Compd., Russ. Acad. Sci., Moscow 117813, Russia; Eng.) -M. Paetzel 46-102

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Synthesis of P‐Stereogenic Phosphoramidite and Phosphorodiamidite Ligands and Their Application in Asymmetric Catalysis

2015

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A series of P‐stereogenic monodentate phosphoramidite (PNO2) and phosphorodiamidite (PN2O) ligands based on chiral Betti bases has been prepared by modular synthetic procedures. The chirality at the phosphorus can be controlled to a large extent by the synthetic route, leading to stereoselective access to single P‐epimers. The absolute configuration of the P‐atom was assigned by X‐ray diffraction analysis. The new ligands were evaluated in asymmetric catalysis and the influence of the exocyclic amine or alcohol moiety as well as the interplay between the P‐chirality and the stereocenters in the backbone were investigated. Enantioselectivities of up to 85 and 83 % ee were obtained in the Rh‐catalyzed hydrogenation of dimethyl itaconate and in the Pd‐catalyzed allylic amination of (rac)‐(E)‐1,3‐diphenylallyl acetate with benzylamine, respectively. In the Ni‐catalyzed hydrovinylation of styrene, ee values of up to 68 %, excellent chemoselectivities, and high activities (TOFav up to 3000 h–1) were achieved.

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Chiral P*-monodentate phosphite ligand for Pd-catalysed asymmetric allylation reactions

Cited by 6 publications

References 19 publications

P‐Chiral Monodentate Diamidophosphites − New and Efficient Ligands for Palladium‐Catalysed Asymmetric Allylic Substitution

P‐Chiral Monodentate Diamidophosphites − New and Efficient Ligands for Palladium‐Catalysed Asymmetric Allylic Substitution

Chiral P*‐Monodentate Phosphite Ligand for Pd‐Catalyzed Asymmetric Allylation Reactions.

Synthesis of P‐Stereogenic Phosphoramidite and Phosphorodiamidite Ligands and Their Application in Asymmetric Catalysis

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