Pyridinium 1,1'-Binaphthyl-2,2'-disulfonates as Highly Effective Chiral Brønsted Acid-Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction
Manabu Hatano; Toshikatsu Maki; Katsuhiko Moriyama; Manabu Arinobe; Kazuaki Ishihara; Journal of the American Chemical Society 130 (2008) 16858–16860; doi:10.1021/ja806875c

data_4108830
_publ_section_title
;
 Pyridinium 1,1'-Binaphthyl-2,2'-disulfonates as Highly Effective Chiral
 Br\/onsted Acid-Base Combined Salt Catalysts for Enantioselective
 Mannich-Type Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16858
_journal_page_last               16860
_journal_paper_doi               10.1021/ja806875c
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration (S)
_chemical_formula_sum            'C20 H20 Br N O5'
_chemical_formula_weight         434.28
_chemical_name_common
;
[2-Acetyl-1-(4-bromo-phenyl)-2-hydroxy-3-oxo-butyl]
-carbamic acid benzyl ester
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   6.001(5)
_cell_length_b                   10.898(5)
_cell_length_c                   29.128(5)
_cell_measurement_temperature    173(2)
_cell_volume                     1904.9(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            13697
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.189
_exptl_absorpt_correction_T_max  0.6686
_exptl_absorpt_correction_T_min  0.5596
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                4218
_reflns_number_total             4714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja806875c_si_003.cif
_cod_data_source_block           morib1
_cod_database_code               4108830