Chiral Brønsted acid-catalyzed enantioselective addition of indoles to ketimines.
Kano, Taichi; Takechi, Ryosuke; Kobayashi, Ryohei; Maruoka, Keiji; Organic & biomolecular chemistry 12 (2014) 724–727; doi:10.1039/c3ob42190b

data_7153602
_publ_section_title
;
 Chiral Br\/onsted acid-catalyzed enantioselective addition of indoles to
 ketimines.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              724
_journal_page_last               727
_journal_paper_doi               10.1039/c3ob42190b
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H17 Br N2 O4'
_chemical_formula_sum            'C20 H17 Br N2 O4'
_chemical_formula_weight         429.27
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.3592(13)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.24936(19)
_cell_length_b                   10.4306(2)
_cell_length_c                   9.62893(18)
_cell_measurement_reflns_used    7904
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.34
_cell_measurement_theta_min      4.24
_cell_volume                     916.60(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8128
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.314
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.480
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1223 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                2703
_reflns_number_total             3005
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c3ob42190b.txt
_cod_data_source_block           3409-5
_cod_original_cell_volume        916.59(4)
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