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First quinine-based aryl phosphite: synthesis and application in the Pd-catalyzed enantioselective rearrangement of allylic thiocarbamate

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Abstract

New quinine-based polyfunctional aryl phosphite was synthesized. The phosphorus center in the new compound is characterized by a large cone angle (θ = 190°). The new compound can be used in the Pd-catalyzed enantioselective rearrangement of cyclic O-allylic thiocarbamate into S-allylic thiocarbamate in an optical yield of up to 47% with a quantitative conversion.

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Authors and Affiliations

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

    O. G. Bondarev, V. N. Tsarev & V. A. Davankov

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

    K. N. Gavrilov

  3. Rheno-Westphalian University of Technology in Aachen, Institute of Organic Chemistry, Professor Pirlet str. 1, D-52056, Aachen, Germany

    H.-J. Gais

Authors
  1. O. G. Bondarev
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  2. K. N. Gavrilov
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  3. V. N. Tsarev
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  4. V. A. Davankov
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  5. H.-J. Gais
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Bondarev, O.G., Gavrilov, K.N., Tsarev, V.N. et al. First quinine-based aryl phosphite: synthesis and application in the Pd-catalyzed enantioselective rearrangement of allylic thiocarbamate. Russian Chemical Bulletin 51, 1748–1750 (2002). https://doi.org/10.1023/A:1021324126769

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  • DOI: https://doi.org/10.1023/A:1021324126769

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