Effect of Chiral Diene Ligands in Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Sulfonyl Compounds
Takahiro Nishimura; Yuka Takiguchi; Tamio Hayashi; Journal of the American Chemical Society 134 (2012) 9086–9089; doi:10.1021/ja303109q

data_4118019
_publ_section_title
;
 Effect of Chiral Diene Ligands in Rhodium-Catalyzed Asymmetric Addition
 of Arylboronic Acids to \a,\b-Unsaturated Sulfonyl Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9086
_journal_page_last               9089
_journal_paper_doi               10.1021/ja303109q
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H20 Cl2 O3 S'
_chemical_formula_weight         435.34
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.653(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8331(3)
_cell_length_b                   12.3566(4)
_cell_length_c                   16.8282(6)
_cell_measurement_reflns_used    11626
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.58
_cell_volume                     2040.53(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.1540
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16053
_diffrn_reflns_theta_full        59.99
_diffrn_reflns_theta_max         59.99
_diffrn_reflns_theta_min         4.44
_exptl_absorpt_coefficient_mu    3.990
_exptl_absorpt_correction_T_max  0.8254
_exptl_absorpt_correction_T_min  0.4354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Higashi, T. (1995). 
 Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         5516
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1778
_refine_ls_R_factor_gt           0.0990
_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^)+(0.1241P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.2776
_reflns_number_gt                2841
_reflns_number_total             5516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303109q_si_002.cif
_cod_data_source_block           4bv
_cod_original_sg_symbol_Hall     P2yb
_cod_database_code               4118019