K. N. Gavrilov, I. V. Chuchelkin, A. A. Shiryaev, I. D. Firsin, V. M. Trunina, V. K. Gavrilov, Ya. P. Bityak, D. A. Fedorov, V. S. Zimarev, N. S. Goulioukina, “TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions”, Mendeleev Commun., 2023, Volume 33, Issue 6,Pages 776

This article is cited in 1 paper

Communications

TADDOL-based P,S-bidentate diastereomeric ligands in asymmetric allylation and hydrogenation reactions

K. N. Gavrilov^a, I. V. Chuchelkin^a, A. A. Shiryaev^bc, I. D. Firsin^a, V. M. Trunina^a, V. K. Gavrilov^a, Ya. P. Bityak^d, D. A. Fedorov^d, V. S. Zimarev^ae, N. S. Goulioukina^aef

^a Department of Chemistry, S.A. Esenin Ryazan State University, Ryazan, Russian Federation
^b I.P. Pavlov Ryazan State Medical University, Ryazan, Russian Federation
^c Scientific, Educational and Innovation Center for Chemical and Pharmaceutical Technologies, B.N. Yeltsin Ural Federal University, Ekaterinburg, Russian Federation
^d Moscow Institute of Physics and Technology (National Research University), Dolgoprudny, Moscow Region, Russian Federation
^e Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
^f A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: Diastereomeric P,S-bidentate phosphoramidite ligands with TADDOL core and (1R,2S)-1,2-diphenyl-2-(phenylthio)-ethan-1-amine residue were synthesized. These ligands provided up to 76% ee in the Pd-catalyzed alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate, up to 70% ee in the amination of this substrate with pyrrolidine, and 89–95% ee in the Rh-catalyzed asymmetric hydro- genation of dimethyl itaconate and methyl (Z)-2-acetamido-3-arylacrylates. The different contributions of diastereomeric chiral inducers to the catalytic outcome are discussed.

Keywords: asymmetric catalysis, allylic substitution, palladium, hydrogenation, rhodium, phosphoramidites, P,S-ligands.

Language: English

DOI: 10.1016/j.mencom.2023.10.012

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