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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 23
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Original Articles

Palladium-Catalyzed Diastereoselective Synthesis of Isoindolinones

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Pages 4141-4158 | Published online: 22 Aug 2006

References

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  • Thebtaranonth , C. and Thebtaranonth , Y. 1994 . “Cyclization Reaction,” , London : CRC Press .
  • Tsuji , J. 1995 . “Palladium Reagents and Catalysts,” , Chichester : Wiley .
  • For the synthesis of isoindolinones via, transition metal-catalyzed carbonylative cyclizations: Bird C. W. J. Organomet. Chem. 1973 47 296
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  • Cho , C. S. , Jiang , L. H. , Lee , D. Y. , Shim , S. C. , Lee , H. S. and Cho , S.-D. J. Heterocyclic Chem. , in press.
  • Crystal data for 12: C15H13NO2, M, = 217.2595, orthorhombic, a, = 8.094(2), b, = 9.625(2), c, = 14.959(3) Å, V, = 1165.3(4) Å3 (by least-squares analysis of 25 reflections), T, = 294 K, space group P212121 (#19), graphite monochromated Mo-Kα radiation, λ = 0.70930 Å, Z, = 4, Dc, = 1.227 g cm−3, F(000) = 464, a chunky crystal with dimensions 0.20 x 0.20 x 0.32 mm, μ(Mo-Kα) = 0.8 cm−1, semi-empirical absorption correction based on Ψ scans, transmission factors 83.7134–99.8418%; Enraf-Nonius CAD4 diffractometer; 1393 reflections measured, 783 unique reflections with I 3σ(I) were used during subsequent structure refinement. The structure was solved by direct methods (Multan)8 and subsequent Fourier difference techniques, and refined anisotropically, by full-matrix least-squares, on F 2 (program MolEN).9 Hydrogen atoms were included. The weighting scheme was w −1 = σF 2 The final discrepancy indices R, = Σ‖Fo| - |Fc‖/|Fo| and Rw, = (Σw‖Fo| - |Fc‖2/|w|Fo|2)1,2 are 0.0344 and 0.0299, g.o.f. = 0.45.
  • Crystal data for 13: C17H15NO2, M, = 265.3035, orthorhombic, a, = 6.030(4), b, = 13.980(3), c, = 16.774(4) Å, V, = 1414.0(9) Å3 (by least-squares analysis of 25 reflections), T=294 K, space group P212121 (#19), graphite monochromated Mo-Kα radiation, λ = 0.70930 Å, Z, = 4, Dc, = 1.246 g cm−3, F(000) = 560, a needle crystal with dimensions 0.10 x 0.10 x 0.32 mm, μ(Mo-Kα) = 0.8 cm−1, semi-empirical absorption correction based on Ψ scans, transmission factors 94.7552–99.9232%; Enraf-Nonius CAD4 diffractometer; 1700 reflections measured, 737 unique reflections with I, > 3σ(I) were used during subsequent structure refinement. The structure was solved by direct methods (Multan)8 and subsequent Fourier difference techniques, and refined anisotropically, by full-matrix least-squares, on F 2 (program MolEN).9 Hydrogen atoms were included. The weighting scheme was w −1 = σF 2 The final discrepancy indices R, = Σ‖Fo| - |Fc‖/Fo| and Rw, = (Σw‖Fo| - |Fc‖2/Σw|Fo|2)1/2 are 0.0422 and 0.0445, g.o.f. = 1.42.
  • Main , P. , Fiske , S. J. , Hull , S. E. , Lessinger , L. , Germain , G. , Declerg , J. P. and Woolfson , M. M. 1980 . “MULTAN 80,” , University of York .
  • 1990 . “MolEN, An Interactive Structure Solution Procedure,” , Delft , , The Netherlands : Enraf-Nonius .
  • Coperet , C. , Sugihara , G. , Wu , G. , Shimoyama , I. and Negishi , E. 1995 . J. Am. Chem. Soc. , 117 : 3422
  • Shim , S. C. , Lee , D. Y. , Jiang , L. H. , Kim , T. J. and Cho , S.-D. 1995 . J. Heterocyclic Chem. , 32 : 363
  • Marchal , J. , Bodiguel , J. , Fort , Y. and Caubere , P. 1995 . J. Org. Chem. , 60 : 8336
  • Lee , D. Y. , Cho , C. S. , Jiang , L. H. , Wu , X. , Shim , S. C. and Oh , D. H. Synth. Commun. , in press.

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