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. Mikhel^a,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: k.gavrilov@rsu.edu.ru

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

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