Highly enantioselective synthesis of bisoxindoles with two vicinal quaternary stereocenters via Lewis base mediated addition of oxindoles to isatin-derived ketimines.
Tang, Zhongkai; Shi, Yan; Mao, Haibin; Zhu, Xuebin; Li, Weipeng; Cheng, Yixiang; Zheng, Wen-Hua; Zhu, Chengjian; Organic & biomolecular chemistry 12 (2014) 6085–6088; doi:10.1039/c4ob01039f

data_7153916
_publ_section_title
;
 Highly enantioselective synthesis of bisoxindoles with two vicinal
 quaternary stereocenters via Lewis base mediated addition of oxindoles to
 isatin-derived ketimines.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6085
_journal_page_last               6088
_journal_paper_doi               10.1039/c4ob01039f
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C39 H38 Cl2 N3 O6'
_chemical_formula_sum            'C39 H38 Cl2 N3 O6'
_chemical_formula_weight         715.62
_chemical_name_systematic
; 
 ? 
;
_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                 101.1706(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.14509(12)
_cell_length_b                   9.34727(9)
_cell_length_c                   19.6126(3)
_cell_measurement_reflns_used    8437
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      73.3180
_cell_measurement_theta_min      4.4230
_cell_volume                     1824.61(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11295
_diffrn_reflns_theta_full        73.47
_diffrn_reflns_theta_max         73.47
_diffrn_reflns_theta_min         4.44
_exptl_absorpt_coefficient_mu    2.012
_exptl_absorpt_correction_T_max  0.8242
_exptl_absorpt_correction_T_min  0.3138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.592
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         5191
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0942P)^2^+2.9655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                5089
_reflns_number_total             5191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01039f2.cif
_cod_data_source_block           najinguniversity-140113
_cod_depositor_comments          'Adding full bibliography for 7153916.cif.'
_cod_original_cell_volume        1824.60(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7153916