The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids
Jingchao Feng; Wenjin Yan; Dong Wang; Peng Li; Quantao Sun; Rui Wang; Chem.Commun. 48 (2012) 8003–; doi:10.1039/c2cc33200k

data_7108109
_publ_section_title
;
 The highly enantioselective addition of indoles and pyrroles to
 isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids
;
_journal_name_full               Chem.Commun.
_journal_page_first              8003
_journal_paper_doi               10.1039/c2cc33200k
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C23 H23 Br2 N3 O3'
_chemical_formula_weight         549.26
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                   40.74(3)
_cell_length_b                   9.259(6)
_cell_length_c                   12.727(9)
_cell_measurement_reflns_used    3288
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.16
_cell_measurement_theta_min      2.26
_cell_volume                     4801(6)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.1146
_diffrn_reflns_av_sigmaI/netI    0.1311
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32845
_diffrn_reflns_theta_full        24.89
_diffrn_reflns_theta_max         24.89
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    3.405
_exptl_absorpt_correction_T_max  0.6658
_exptl_absorpt_correction_T_min  0.5792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         8254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0156P)^2^+6.3934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                4305
_reflns_number_total             8254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc33200k.txt
_cod_data_source_block           p21212
_cod_original_sg_symbol_H-M      P2(1)2(1)2
_cod_database_code               7108109