Palladium-Catalyzed Asymmetric Benzylation of 3-Aryl Oxindoles
Barry M. Trost; Lara C. Czabaniuk; Journal of the American Chemical Society 132 (2010) 15534–15536; doi:10.1021/ja1079755

data_4103463
_publ_contact_author_address     'Dept. of Chemistry, Stanford University'
_publ_contact_author_email       laracz@stanford.edu
_publ_contact_author_name        'Lara Czabaniuk'
_publ_contact_author_phone       '734 732 3131'
_publ_section_title
;
 Palladium-Catalyzed Asymmetric Benzylation of 3-Aryl Oxindoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15534
_journal_page_last               15536
_journal_paper_doi               10.1021/ja1079755
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H24 Br N O3'
_chemical_formula_sum            'C33 H24 Br N O3'
_chemical_formula_weight         562.44
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0655(7)
_cell_length_b                   10.9316(8)
_cell_length_c                   23.7249(17)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.56
_cell_measurement_theta_min      2.53
_cell_volume                     2610.5(3)
_computing_cell_refinement       'Bruker SAINT v7.68A'
_computing_data_collection       'Bruker APEX-II v2010-7'
_computing_data_reduction        'Bruker SAINT v7.68A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            46357
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    1.611
_exptl_absorpt_correction_T_max  0.9102
_exptl_absorpt_correction_T_min  0.7653
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2674 Friedel pairs'
_refine_ls_abs_structure_Flack   0.005(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0579
_reflns_number_gt                5596
_reflns_number_total             6273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1079755_si_002.cif
_cod_data_source_block           su035
_cod_database_code               4103463