Organocatalytic Enantioselective Michael-Michael-Michael-Aldol Condensation Reactions: Control of Six Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles.
Chaudhari, Prakash D.; Hong, Bor-Cherng; Lee, Gene-Hsiang; Organic letters 19 (2017) 6112–6115; doi:10.1021/acs.orglett.7b02962

data_1547861
_publ_section_title
;
 Organocatalytic Enantioselective Michael-Michael-Michael-Aldol
 Condensation Reactions: Control of Six Stereocenters in a
 Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic
 Oxindoles.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6112
_journal_page_last               6115
_journal_paper_doi               10.1021/acs.orglett.7b02962
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C32 H28 Br2 N2 O4.5'
_chemical_formula_weight         672.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.8598(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.9252(5)
_cell_length_b                   10.3277(2)
_cell_length_c                   12.9767(3)
_cell_measurement_reflns_used    9761
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.10
_cell_measurement_theta_min      4.67
_cell_volume                     3168.18(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10182
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.989
_diffrn_reflns_theta_min         4.672
_exptl_absorpt_coefficient_mu    3.562
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 2668 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.024(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5917
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+1.5115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                5832
_reflns_number_total             5917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02962_si_004.cif
_cod_data_source_block           ic18259
_cod_depositor_comments
'Adding full bibliography for 1547860--1547863.cif.'
_cod_original_formula_sum        'C32 H28 Br2 N2 O4.50'
_cod_database_code               1547861
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.473
_shelx_estimated_absorpt_t_max   0.704
_shelx_res_checksum              36055
_shelx_hkl_checksum              49717