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A first P,N-bidentate phosphite with a chiral ketimine fragment. Catalytic properties of its RhI and PdII complexes in comparison with those of phosphine analogs

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Abstract

A chiral P,N-bidentate aryl phosphite ligand containing peripheral (R)-(+)-camphor-derived ketimine and its rhodium(I) and palladium(II) chelate complexes were synthesized for the first time. These compounds were found to be suitable for asymmetric allylic substitution. The Pd-catalyzed sulfonylation of 1,3-diphenylallyl acetate with sodium p-toluenesulfinate gave the product in 73% ee; in the alkylation of the same substrate with dimethyl malonate, the ee was 94%. These ee values are higher than the enantioselectivity achieved with the known phosphine analogs.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

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

  2. S. A. Esenin Ryazan State Pedagogical University, 46 ul. Svobody, 390000, Ryazan, Russian Federation

    S. V. Zheglov, A. A. Shiryaev & K. N. Gavrilov

Authors
  1. V. N. Tsarev
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  2. S. E. Lyubimov
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  3. S. V. Zheglov
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  4. A. A. Shiryaev
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  5. V. A. Davankov
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  6. K. N. Gavrilov
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1942–1945, September, 2004.

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Tsarev, V.N., Lyubimov, S.E., Zheglov, S.V. et al. A first P,N-bidentate phosphite with a chiral ketimine fragment. Catalytic properties of its RhI and PdII complexes in comparison with those of phosphine analogs. Russ Chem Bull 53, 2025–2028 (2004). https://doi.org/10.1007/s11172-005-0066-1

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  • DOI: https://doi.org/10.1007/s11172-005-0066-1

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