Binaphthol-Derived Bisphosphoric Acids Serve as Efficient Organocatalysts for Highly Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides to Electron-Deficient Olefins
Long He; Xiao-Hua Chen; De-Nan Wang; Shi-Wei Luo; Wen-Quan Zhang; Jie Yu; Lei Ren; Liu-Zhu Gong; Journal of the American Chemical Society 133 (2011) 13504–13518; doi:10.1021/ja204218h

data_4106659
_publ_section_title
;
 Binaphthol-Derived Bisphosphoric Acids Serve as Efficient Organocatalysts
 for Highly Enantioselective 1,3-Dipolar Cycloaddition of Azomethine
 Ylides to Electron-Deficient Olefins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13504
_journal_page_last               13518
_journal_paper_doi               10.1021/ja204218h
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C22 H22 Br N O6'
_chemical_formula_weight         476.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 100.801(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   9.175(5)
_cell_length_b                   8.368(5)
_cell_length_c                   14.289(5)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.6505
_cell_measurement_theta_min      3.1475
_cell_volume                     1077.6(9)
_computing_cell_refinement       'CrysAlis RED'
_computing_data_collection       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8089
_diffrn_reflns_theta_full        62.65
_diffrn_reflns_theta_max         62.65
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    2.930
_exptl_absorpt_correction_T_max  0.5398
_exptl_absorpt_correction_T_min  0.3588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(15)
_refine_ls_extinction_coef       0.0044(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0237P)^2^+0.4506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0586
_reflns_number_gt                3084
_reflns_number_total             3162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja204218h_si_001.cif
_cod_data_source_block           080526-cu
_cod_database_code               4106659