Organocatalytic Synthesis of Spiro[pyrrolidin-3,3'-oxindoles] with High Enantiopurity and Structural Diversity
Xiao-Hua Chen; Qiang Wei; Shi-Wei Luo; Han Xiao; Liu-Zhu Gong; Journal of the American Chemical Society 131 (2009) 13819–13825; doi:10.1021/ja905302f

data_4105070
_publ_section_title
;
 Organocatalytic Synthesis of Spiro[pyrrolidin-3,3'-oxindoles] with High
 Enantiopurity and Structural Diversity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13819
_journal_page_last               13825
_journal_paper_doi               10.1021/ja905302f
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H33 Br N2 O6'
_chemical_formula_weight         585.48
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_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                   9.0746(3)
_cell_length_b                   17.4596(5)
_cell_length_c                   36.6618(10)
_cell_measurement_reflns_used    5568
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      62.7618
_cell_measurement_theta_min      2.4016
_cell_volume                     5808.7(3)
_computing_cell_refinement       'CrysAlis RED'
_computing_data_collection       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1105
_diffrn_reflns_av_sigmaI/netI    0.0996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            27221
_diffrn_reflns_theta_full        61.12
_diffrn_reflns_theta_max         61.12
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_T_max  0.6578
_exptl_absorpt_correction_T_min  0.5879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4326
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0740
_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^)+(0.0492P)^2^+24.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                2204
_reflns_number_total             4326
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja905302f_si_004.cif
_cod_data_source_block           090116
_cod_database_code               4105070