Lewis Acid Promoted Diastereoselective Addition of TMSCN and TMSCF3 to Isatin-Derived N-Sulfinyl Ketimines: Synthesis of Optically Active Tetrasubstituted 3-Aminooxindoles.
Chen, Diao; Xu, Ming-Hua; The Journal of organic chemistry 79 (2014) 7746–7751; doi:10.1021/jo501360g

data_4029836
_publ_section_title
;
 Lewis Acid Promoted Diastereoselective Addition of TMSCN and TMSCF3 to
 Isatin-Derived N-Sulfinyl Ketimines: Synthesis of Optically Active
 Tetrasubstituted 3-Aminooxindoles.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7746
_journal_page_last               7751
_journal_paper_doi               10.1021/jo501360g
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration S
_chemical_formula_sum            'C13 H14 Cl F3 N2 O2 S'
_chemical_formula_weight         354.78
_space_group_IT_number           4
_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                 96.4340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7533(2)
_cell_length_b                   9.4038(2)
_cell_length_c                   14.3130(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1571.99(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14035
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.8858
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.386
_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   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6807
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0332P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                6187
_reflns_number_total             6807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501360g_si_003.cif
_cod_data_source_block           2013178_0m
_cod_depositor_comments
'Adding full bibliography for 4029835--4029836.cif.'
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4029836