Alexei A. Shiryaev

Ural Federal University

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Konstantin N. Gavrilov

Ryazan State University

Sergey V. Zheglov

Ryazan State University

ВА

В. А. Даванков

A. N. Nesmeyanov Institute of Organoelement Compounds

S. E. Lyubimov

A. N. Nesmeyanov Institute of Organoelement Compounds

Ilya V. Chuchelkin

Ryazan State University

Vladislav K. Gavrilov

Ryazan State University

Oleg G. Bondarev

Centre National de la Recherche Scientifique

V. N. Tsarev

Altai State University

Damir A. Safin

Ural Federal University

Maria G. Babashkina

UCLouvain

Cooperative Institutions

Ryazan State University

A. N. Nesmeyanov Institute of Organoelement Compounds

Russian Academy of Sciences

Lomonosov Moscow State University

N.D. Zelinsky Institute of Organic Chemistry

Frumkin Institute of Physical Chemistry and Electrochemistry

Moscow State University

Ryazan Institute of Management and Law

Jagiellonian University

Kurgan State University

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Easily Accessible Chiral P,N-Bidentate Aryl Phosphites, Their Complexation and Application in Enantioselective Allylic Alkylation, Sulfonylation and Hydrosilylation

European Journal of Inorganic Chemistry (2002)

Konstantin N. Gavrilov Oleg G. Bondarev R. V. Lebedev Alexei A. Shiryaev S. E. Lyubimov

New chiral P,N-hybrid aryl phosphites have been obtained by one-step phosphorylation of amino and imino alcohols. Complexation of the new ligands with [Rh(CO)2Cl]2, [Pd(COD)Cl2] and [Pd(allyl)Cl]2 was found to give chelate complexes [Rh(CO)Cl(η2-P∩N)], [PdCl2(η2-P∩N)] and [Pd(allyl)(η2-P∩N)]+Cl−, respectively. With these new P,N-ligands, up to 82% ee enantioselectivity was achieved in the Pd-catalysed alkylation of ethyl 3-penten-2-yl carbonate with dimethyl malonate, up to 80% ee in the Pd-catalysed sulfonylation of methyl 3-penten-2-yl carbonate with sodium p-toluenesulfinate, and up to 50% ee in the Rh-catalysed hydrosilylation of acetophenone with diphenylsilane. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

Hydrosilylation

Acetophenone

Tsuji–Trost reaction

Dimethyl malonate

10.1002/1099-0682(200206)2002:6<1367::aid-ejic1367>3.3.co;2-6

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Citations (0)

Application of mixed phosphorus/sulfur ligands based on terpenoids to Pd-catalyzed asymmetric allylic substitution and Rh-catalyzed hydrogenation

Organic & Biomolecular Chemistry (2024)

Konstantin N. Gavrilov Ilya V. Chuchelkin Vladislav K. Gavrilov Ilya D. Firsin Valeria M. Trunina

A small library of easily prepared diamidophosphite-sulfides based on 1,3-thioether alcohols, primarily of terpenoid nature, was developed. Upon complexation with Pd(II) ions, these hemilabile ligands showed the ability to form both

Substitution (logic)

10.1039/d4ob00840e

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Iminophosphites as new chiral P,N-bidentate ligands

Mendeleev Communications (2001)

Konstantin N. Gavrilov Alexei I. Polosukhin Oleg G. Bondarev A.V. Korostylev S. E. Lyubimov

10.1070/mc2001v011n01abeh001356

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Citations (5)

Nonsimple relationships between the P∗-chiral diamidophosphite and the arylphosphine moieties in Pd-catalyzed asymmetric reactions: combinatorial approach and P,P∗-bidentate phosphine-diamidophosphites

Tetrahedron (2013)

Konstantin N. Gavrilov Alexei A. Shiryaev Sergey V. Zheglov Vladislav K. Gavrilov Nikolay N. Groshkin

Desymmetrization

Stereocenter

10.1016/j.tet.2013.12.006

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Citations (18)

Pd-catalyzed asymmetric reactions using resorcinol- and hydroquinone-based P∗,P∗-bidentate diamidophosphites

Tetrahedron Letters (2010)

Konstantin N. Gavrilov Sergey V. Zheglov Alexei A. Shiryaev Nikolay N. Groshkin E. A. Rastorguev

Resorcinol

Hydroquinone

10.1016/j.tetlet.2010.11.111

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Citations (14)

CCDC 1938921: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Dinara S. Shapenova Alexei A. Shiryaev Michael Bolte Mercedes Kukułka Dariusz W. Szczepanik

10.5517/ccdc.csd.cc232lvn

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Diamidophosphites with P*-stereocentres and their performance in metal-catalyzed enantioselective reactions

Phosphorus, sulfur, and silicon and the related elements (2019)

Alexei A. Shiryaev Konstantin N. Gavrilov Sergey V. Zheglov Vladislav K. Gavrilov Ilya V. Chuchelkin

In this mini-review, the application of P*-chiral diamidophosphites in metal-catalyzed asymmetric reactions. These ligands demonstrate moderate to high levels of asymmetric induction in Pd-catalyzed enantioselective allylations of (E)-1,3-diphenylallyl acetate, desymmetrizations of N,N’-ditosyl-meso-cyclopent-4-ene-1,3-diol bis-carbamate, in the asymmetric construction of quaternary carbon stereocenters and Rh-catalyzed hydrogenation of (Z)-methyl 2-acetamido-3-phenylacrylate.

Stereocenter

Quaternary carbon

Carbamate

10.1080/10426507.2018.1543300

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Citations (0)

Russian Journal of Coordination Chemistry (2001)

A.I. Polosukhin Oleg G. Bondarev S. E. Lyubimov Alexei A. Shiryaev P. V. Petrovskii

10.1023/a:1011362030475

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Citations (9)

NovelP,N-bidentate phosphite ligands in asymmetric catalysis

Chirality (2003)

Konstantin N. Gavrilov Oleg G. Bondarev A.V. Korostylev Alexei I. Polosukhin Vassily N. Tsarev

Results achieved by the authors in the synthesis of chiral P,N-phosphite ligands are summarized. Three groups of new chiral P,N-phosphites are discussed, namely, ligands derived from 1,1'-bi-2-naphthol, ligands possessing an acyclic phosphorus center, and P*-chiral ligands derived from (S)-2-anilinomethylpyrrolidine. An overview of complexation of the ligands with Rh(I) and Pd(II) precursors is given. Accessibility and stability of chiral phosphite ligands possessing acyclic phosphorus was analyzed for the first time along with their efficiency in terms of stereoselectivity. The title ligands are shown to be highly efficient in the Pd-catalyzed allylic alkylation (up to 85% ee) and, especially, allylic sulfonylation (up to 97% ee) reactions in certain cases outperformed all known catalytic systems.

10.1002/chir.10258

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Citations (10)

Easily Accessible ChiralP,N-Bidentate Aryl Phosphites, Their Complexation and Application in Enantioselective Allylic Alkylation, Sulfonylation and Hydrosilylation

European Journal of Inorganic Chemistry (2002)

Konstantin N. Gavrilov Oleg G. Bondarev R. V. Lebedev Alexei A. Shiryaev S. E. Lyubimov

Hydrosilylation

Acetophenone

Tsuji–Trost reaction

Dimethyl malonate

10.1002/1099-0682(200206)2002:6<1367::aid-ejic1367>3.0.co;2-f

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Citations (31)