Enantioselective Synthesis of Quaternary 3-Aminooxindoles via Organocatalytic Asymmetric Michael Addition of 3-Monosubstituted 3-Aminooxindoles to Nitroolefins
Bao-Dong Cui; Wen-Yong Han; Zhi-Jun Wu; Xiao-Mei Zhang; Wei-Cheng Yuan; Journal of Organic Chemistry 78 (2013) 8833–8839; doi:10.1021/jo401154b

data_4028528
_publ_section_title
;
 Enantioselective Synthesis of Quaternary 3-Aminooxindoles via
 Organocatalytic Asymmetric Michael Addition of 3-Monosubstituted
 3-Aminooxindoles to Nitroolefins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8833
_journal_page_last               8839
_journal_paper_doi               10.1021/jo401154b
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N3 O5 S'
_chemical_formula_sum            'C18 H19 N3 O5 S'
_chemical_formula_weight         389.42
_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                 98.0370(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3672(7)
_cell_length_b                   8.7128(7)
_cell_length_c                   12.7310(11)
_cell_measurement_reflns_used    4049
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.75
_cell_volume                     919.00(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9815
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4943
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0406P)^2^+0.0951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                4390
_reflns_number_total             4943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401154b_si_002.cif
_cod_data_source_block           mo_wb_cbd_1_sad
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028528