Abstract:
A novel P*,S-bidentate diamidophosphite ligand with a 1,3,2-diazaphospholidine core and an exocyclic thioether fragment provided up to 86% ee in the Pd-catalyzed alkylation of rac-(E)-1,3-diphenylallyl acetate with dimethyl malonate, as well as up to 73 and 75% ee in the amination of this substrate with pyrrolidine and diethyl (aminomethyl)phosphonate, respectively. For the Pd-catalyzed alkylation of cinnamyl acetate with β-keto esters, ee values up to 76% were achieved.
Citation:
K. N. Gavrilov, I. V. Chuchelkin, S. V. Zheglov, I. D. Firsin, V. S. Zimarev, V. K. Gavrilov, A. V. Maximychev, A. M. Perepukhov, N. S. Goulioukina, “First P*,S-bidentate diamidophosphite ligand in Pd-catalyzed asymmetric reactions”, Mendeleev Commun., 30:1 (2020), 31–33
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https://www.mathnet.ru/eng/mendc1091
https://www.mathnet.ru/eng/mendc/v30/i1/p31
This publication is cited in the following 13 articles:
Konstantin N. Gavrilov, Ilya V. Chuchelkin, Vladislav K. Gavrilov, Ilya D. Firsin, Valeria M. Trunina, Alexey A. Shiryaev, Alena O. Shkirdova, Evgeniya V. Bermesheva, Victor A. Tafeenko, Vladimir V. Chernyshev, Vladislav S. Zimarev, Nataliya S. Goulioukina, “Application of mixed phosphorus/sulfur ligands based on terpenoids in Pd-catalyzed asymmetric allylic substitution and Rh-catalyzed hydrogenation”, Org. Biomol. Chem., 22:31 (2024), 6362
K. N. Gavrilov, I. V. Chuchelkin, V. M. Trunina, B. K. Gavrilov, I. D. Firsin, E. S. Rud, V. A. Tafeenko, E. V. Bermesheva, “Complexation with PdII and enantioselective allylic amination using new P*-monodentane bicyclic amidophosphite”, Russ Chem Bull, 73:3 (2024), 574
Stéphane Bellemin-Laponnaz, Thierry Achard, “Recent Progress in Developing Thioether-Containing Ligands for Catalysis Applications”, Synthesis, 56:09 (2024), 1369
V. S. Zimarev, I. V. Chuchelkin, K. N. Gavrilov, I. A. Zamilatskov, V. A. Tafeenko, B. V. Lokshin, N. S. Goulioukina, “Neutral dinuclear palladium(II) complex containing chiral P,S-bridging diamidophosphite-thioether ligands”, Mendeleev Commun., 34:2 (2024), 195–197
Konstantin N. Gavrilov, Ilya V. Chuchelkin, Vladislav K. Gavrilov, Sergey V. Zheglov, Ilya D. Firsin, Valeria M. Trunina, Nataliya E. Borisova, Yan P. Bityak, Olga A. Maloshitskaya, Victor A. Tafeenko, Vladislav S. Zimarev, Nataliya S. Goulioukina, “Hemilabile Diamidophosphite-Thioether Ligands with a β-Hydroxy Sulfide Backbone: Palladium(II) Complexes and Asymmetric Allylic Substitution”, Organometallics, 42:15 (2023), 1985
K. N. Gavrilov, I. V. Chuchelkin, V. K. Gavrilov, V. M. Trunina, I. D. Firsin, S. V. Zheglov, Ya. P. Bityak, D. A. Fedorov, V. S. Zimarev, N. S. Goulioukina, “P*,S-Bidentate diamidophosphite based on 3-(phenylthiomethyl)phenol”, Russ Chem Bull, 72:5 (2023), 1251
K. N. Gavrilov, I. V. Chuchelkin, V. M. Trunina, V. K. Gavrilov, I. D. Firsin, E. V. Bermesheva, “P*,N-Bidentate bicyclic phosphoramidite: synthesis and catalytic testing”, Russ Chem Bull, 72:4 (2023), 873
I. D. Firsin, I. V. Chuchelkin, V. K. Gavrilov, V. M. Trunina, V. S. Zimarev, S. V. Zheglov, K. N. Gavrilov, N. S. Goulioukina, “Chiral P*,S-bidentate diamidophosphites with 1,2-thioether alcohol–based exocyclic substituents in asymmetric Pd-catalyzed reactions”, Phosphorus, Sulfur, and Silicon and the Related Elements, 197:5-6 (2022), 518
Mariette M. Pereira, Rui M. B. Carrilho, Mário J. F. Calvete, Organophosphorus Chemistry, 2022, 62
Ilya V. Chuchelkin, Konstantin N. Gavrilov, Vladislav K. Gavrilov, Sergey V. Zheglov, Ilya D. Firsin, Alexander M. Perepukhov, Alexander V. Maximychev, Nataliya E. Borisova, Ilya A. Zamilatskov, Vladimir S. Tyurin, Catherine Dejoie, Vladimir V. Chernyshev, Vladislav S. Zimarev, Nataliya S. Goulioukina, “Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols”, Organometallics, 40:21 (2021), 3645
Jèssica Margalef, Maria Biosca, Pol de la Cruz Sánchez, Jorge Faiges, Oscar Pàmies, Montserrat Diéguez, “Evolution in heterodonor P-N, P-S and P-O chiral ligands for preparing efficient catalysts for asymmetric catalysis. From design to applications”, Coordination Chemistry Reviews, 446 (2021), 214120
Ilya V. Chuchelkin, Konstantin N. Gavrilov, Nataliya E. Borisova, Alexander M. Perepukhov, Alexander V. Maximychev, Sergey V. Zheglov, Vladislav K. Gavrilov, Ilya D. Firsin, Vladislav S. Zimarev, Igor S. Mikhel, Victor A. Tafeenko, Elena V. Murashova, Vladimir V. Chernyshev, Nataliya S. Goulioukina, “Diamidophosphites from β-hydroxyamides: readily assembled ligands for Pd-catalyzed asymmetric allylic substitution”, Dalton Trans., 49:17 (2020), 5625
Jèssica Margalef, Oscar Pàmies, Miquel A. Pericàs, Montserrat Diéguez, “Evolution of phosphorus–thioether ligands for asymmetric catalysis”, Chem. Commun., 56:74 (2020), 10795
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