Organocatalytic Asymmetric Michael Addition of Oxindoles to Nitroolefins for the Synthesis of 2,2-Disubstituted Oxindoles Bearing Adjacent Quaternary and Tertiary Stereocenters
Cheng-Yong Jin; Yao Wang; Yao-Zong Liu; Chao Shen; Peng-Fei Xu; Journal of Organic Chemistry 77 (2012) 11307–11312; doi:10.1021/jo301886j

data_4027777
_publ_section_title
;
 Organocatalytic Asymmetric Michael Addition of Oxindoles to Nitroolefins
 for the Synthesis of 2,2-Disubstituted Oxindoles Bearing Adjacent
 Quaternary and Tertiary Stereocenters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11307
_journal_page_last               11312
_journal_paper_doi               10.1021/jo301886j
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration none
_chemical_formula_sum            'C20 H17 Br N2 O6'
_chemical_formula_weight         461.27
_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                 105.88(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.60(3)
_cell_length_b                   9.57(3)
_cell_length_c                   17.72(5)
_cell_measurement_reflns_used    1881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.61
_cell_measurement_theta_min      2.31
_cell_volume                     2055(10)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.1767
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7341
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_T_max  0.7634
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         6363
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                3002
_reflns_number_total             6363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301886j_si_002.cif
_cod_data_source_block           p21
_cod_database_code               4027777