Synthesis of enantiomerically enriched 3-amino-2-oxindoles through a palladium-mediated asymmetric intramolecular arylation of α-ketimino amides.
Tolstoy, Päivi; Lee, Samantha X. Y.; Sparr, Christof; Ley, Steven V.; Organic letters 14 (2012) 4810–4813; doi:10.1021/ol302119j

data_1508641
_publ_section_title
;
 Synthesis of enantiomerically enriched 3-amino-2-oxindoles through a
 palladium-mediated asymmetric intramolecular arylation of \a-ketimino
 amides.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4810
_journal_page_last               4813
_journal_paper_doi               10.1021/ol302119j
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration
;
 Flack parameter 0.007(6)
;
_chemical_formula_moiety         'C27 H19 Br N2 O2'
_chemical_formula_sum            'C27 H19 Br N2 O2'
_chemical_formula_weight         483.35
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 94.411(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5078(3)
_cell_length_b                   9.4222(2)
_cell_length_c                   18.6676(6)
_cell_measurement_reflns_used    9048
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2193.48(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14220
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         8841
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                5730
_reflns_number_total             8841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302119j_si_001.cif
_cod_data_source_block           sl1232
_cod_original_cell_volume        2193.5(1)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1508641