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Complexation and Pd-Catalyzed Asymmetric Allylation with Participation of Chiral Ferrocenyliminophosphites

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Abstract

Chiral ferrocene-containing iminoarylphosphite ligands based on 4,4′-dimethoxy-6,6′-di-tert-butyl-biphenyldiol-2,2′ and their chelate complexes with Rh(I) and Pd(II) were synthesized for the first time. They were shown to be perspective reagents in the reactions of asymmetric allyl substitution. The Pd-catalyzed alkylation of 1,3-diphenylallylacetate with dimethyl malonate results in a 87% enantiomer excess (ee), while in sulfonylation of 1,3-diphenylallylacetate with sodium para-toluenesulfinite, this figure amounts to 67%. The results obtained were compared with coordination and catalytic efficiency of a less sterically hindered ferro-cenyliminophosphite based on pyrocatechol. The compositions and structures of new compounds were determined by the 1H, 13C, 31P NMR, IR, mass spectrometry (EI, FAB, and electrospray techniques), and elemental analysis.

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Authors and Affiliations

  1. Esenin State Pedagogical University, ul. Svobody 46, Ryazan, 390000, Russia

    K. N. Gavrilov & S. V. Zheglov

  2. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    V. N. Tsarev, S. E. Lubimov & V. A. Davankov

Authors
  1. K. N. Gavrilov
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  2. V. N. Tsarev
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  3. S. E. Lubimov
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  4. S. V. Zheglov
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  5. V. A. Davankov
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Gavrilov, K.N., Tsarev, V.N., Lubimov, S.E. et al. Complexation and Pd-Catalyzed Asymmetric Allylation with Participation of Chiral Ferrocenyliminophosphites. Russian Journal of Coordination Chemistry 30, 685–691 (2004). https://doi.org/10.1023/B:RUCO.0000043891.44863.9e

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  • DOI: https://doi.org/10.1023/B:RUCO.0000043891.44863.9e

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