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Russian Chemical Bulletin

, Volume 61, Issue 10, pp 1925–1932 | Cite as

Pd-Catalyzed asymmetric transformations involving P*-mono- and P*,N-bidentate diamidophosphites derived from (2S,3S)-N 2,3-dimethyl-N 1-phenylpentane-1,2-diamine

  • K. N. Gavrilov
  • I. V. Chuchelkin
  • S. V. Zheglov
  • A. A. Shiryaev
  • O. V. Potapova
  • I. M. Novikov
  • E. A. Rastorguev
  • P. V. Petrovskii
  • V. A. Davankov
Full Articles

Abstract

The synthesis of new P*-mono- and P*,N-bidentate diamidophosphites, containing 1,3,2-diazaphospholidine rings formed starting from (2S,3S)-N 2,3-dimethyl-N 1-phenylpentane-1,2-diamine, is described. Comparison of their efficiency in the Pd-catalyzed enantioselective allylation with (E)-1,3-diphenylallyl acetate showed that up to 97% ee was reached in the reaction involving dimethyl malonate as a C-nucleophile. The Pd-catalyzed desymmetrization of N,N′-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate gave up to 61% ee.

Key words

diamidophosphites 1,3,2-diazaphospholidines palladium catalysts asymmetric allylation desymmetrization 

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Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • K. N. Gavrilov
    • 1
  • I. V. Chuchelkin
    • 1
  • S. V. Zheglov
    • 1
  • A. A. Shiryaev
    • 1
  • O. V. Potapova
    • 1
  • I. M. Novikov
    • 1
  • E. A. Rastorguev
    • 2
  • P. V. Petrovskii
    • 2
  • V. A. Davankov
    • 2
  1. 1.S. A. Esenin Ryazan State UniversityRyazanRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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