Enantioselective Synthesis of Multisubstituted Biaryl Skeleton by Chiral Phosphoric Acid Catalyzed Desymmetrization/Kinetic Resolution Sequence
Keiji Mori; Yuki Ichikawa; Manato Kobayashi; Yukihiro Shibata; Masahiro Yamanaka; Takahiko Akiyama; Journal of the American Chemical Society 135 (2013) 3964–3970; doi:10.1021/ja311902f

data_4119451
_publ_section_title
;
 Enantioselective Synthesis of Multisubstituted Biaryl Skeleton by Chiral
 Phosphoric Acid Catalyzed Desymmetrization/Kinetic Resolution Sequence
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3964
_journal_page_last               3970
_journal_paper_doi               10.1021/ja311902f
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C37 H27 Br O5'
_chemical_formula_weight         631.50
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.466(4)
_cell_angle_beta                 73.382(4)
_cell_angle_gamma                82.855(4)
_cell_formula_units_Z            2
_cell_length_a                   10.078(4)
_cell_length_b                   10.294(4)
_cell_length_c                   15.787(6)
_cell_measurement_reflns_used    6245
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.20
_cell_volume                     1502.8(10)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16787
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    1.411
_exptl_absorpt_correction_T_max  0.8717
_exptl_absorpt_correction_T_min  0.8162
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     779
_refine_ls_number_reflns         12824
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0110P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                10333
_reflns_number_total             12824
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311902f_si_005.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1502.9(10)
_cod_original_sg_symbol_H-M      'P 1 '
_cod_database_code               4119451