Simple Branched Sulfur-Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters
Hui Wang; Tao Jiang; Ming-Hua Xu; Journal of the American Chemical Society 135 (2013) 971–974; doi:10.1021/ja3110818

data_4119214
_publ_section_title
;
 Simple Branched Sulfur-Olefins as Chiral Ligands for Rh-Catalyzed
 Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective
 Construction of Tetrasubstituted Carbon Stereocenters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              971
_journal_page_last               974
_journal_paper_doi               10.1021/ja3110818
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C40 H34 N2 O8 S2'
_chemical_formula_weight         734.81
_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                80.212(2)
_cell_angle_beta                 71.388(2)
_cell_angle_gamma                75.303(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6190(9)
_cell_length_b                   9.0133(9)
_cell_length_c                   12.6557(13)
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.313
_cell_measurement_theta_min      4.694
_cell_volume                     897.00(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5457
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33606
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.165
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.163
_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   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         4371
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0608P)^2^+0.0724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                4085
_reflns_number_total             4371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3110818_si_002.cif
_cod_data_source_block           cd212342
_cod_database_code               4119214