Enantioselective and Solvent-Controlled Diastereoselective Mannich Reaction of Isatin Imines with Hydroxyacetone: Synthesis of 3-Substituted 3-Aminooxindoles
Qi-Xiang Guo; Yu-Wan Liu; Xing-Cheng Li; Ling-Zhi Zhong; Yun-Gui Peng; Journal of Organic Chemistry 77 (2012) 3589–3594; doi:10.1021/jo202585w

data_4027099
_publ_section_title
;
 Enantioselective and Solvent-Controlled Diastereoselective Mannich
 Reaction of Isatin Imines with Hydroxyacetone: Synthesis of 3-Substituted
 3-Aminooxindoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3589
_journal_page_last               3594
_journal_paper_doi               10.1021/jo202585w
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration unknown
_chemical_formula_moiety         'C26 H25 Br N2 O6 S, 3(H2 O)'
_chemical_formula_sum            'C26 H31 Br N2 O9 S'
_chemical_formula_weight         627.50
_space_group_IT_number           80
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I 4bw'
_symmetry_space_group_name_H-M   'I 41'
_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            8
_cell_length_a                   20.639(11)
_cell_length_b                   20.639(11)
_cell_length_c                   13.164(7)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.79
_cell_volume                     5607(5)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       '\f and \w 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    0.0647
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9418
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    1.595
_exptl_absorpt_correction_T_max  0.8316
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       Block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.062(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1308P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1922
_reflns_number_gt                3140
_reflns_number_total             4254
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202585w_si_002.cif
_cod_data_source_block           mo_20110410b_0m
_cod_original_cell_volume        5608(5)
_cod_database_code               4027099