Palladium-Catalyzed Diastereoselective Synthesis of Isoindolinones

Abstract

Abstract: 2-Bromobenzaldehyde reacts diastereoselectively with chiral alkanolamines under carbon monoxide in the presence of a catalytic amount of bis(triphenylphosphine)palladium(II) chloride to afford the corresponding tricyclic isoindolinones in moderate to good yields.

Notes

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) ų (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.