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ISSN 1998-9539

Application of Hydroxyporphyrins-Based Phosphite-Type Ligands to Asymmetric Pd-Catalyzed Allylic Substitution Reactions

Konstantin N. Gavrilov,a@ Sergey V. Zheglov,a Marina G. Maksimova,a Ilya V. Chuchelkin,a Ivan M. Novikov,a Gelii V. Ponomarev,a,с Dina R. Erzina,a,b and Igor S. Mikhela,b
aS.A. Esenin Ryazan State University, 390000 Ryazan, Russian Federation
bA.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 119071 Moscow, Russian Federation
cV.N. Orekhovich Institute of Biomedical Chemistry, 119121 Moscow, Russian Federation
@Corresponding author E-mail:
Diamidophosphite and phosphite ligands with (S)-2-(anilinomethyl)pyrrolidine or (Sa)-BINOL backbone and porphyrin cores were obtained. The use of these ligands provides up to 92 % ee (enantiomeric excess) in Pd-catalyzed asymmetric alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate, up to 82 % ee in its sulfonylation with sodium p-toluene sulfinate and up to 76 % ee in its amination with pyrrolidine. Also, up to 90 % ee was achieved in Pd-catalyzed allylic alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate. The influence of the structural moieties such as the nature of phosphorus-containing ring or porphyrin exocyclic substituent on the catalytic activity and enantioselectivity are discussed.



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