Exploiting the Modularity of Ion-Paired Chiral Ligands for Palladium-Catalyzed Enantioselective Allylation of Benzofuran-2(3H)-ones
Kohsuke Ohmatsu; Mitsunori Ito; Tomoatsu Kunieda; Takashi Ooi; Journal of the American Chemical Society 135 (2013) 590–593; doi:10.1021/ja312125a

data_4119204
_publ_section_title
;
 Exploiting the Modularity of Ion-Paired Chiral Ligands for
 Palladium-Catalyzed Enantioselective Allylation of Benzofuran-2(3H)-ones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              590
_journal_page_last               593
_journal_paper_doi               10.1021/ja312125a
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration S
_chemical_formula_sum            'C23 H23 Cl O4'
_chemical_formula_weight         398.86
_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                90.00
_cell_angle_beta                 90.982(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   6.4664(7)
_cell_length_b                   24.377(3)
_cell_length_c                   20.197(2)
_cell_measurement_reflns_used    3578
_cell_measurement_temperature    153
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.62
_cell_volume                     3183.2(6)
_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      153
_diffrn_detector_area_resol_mean 8.366[pixels/mm]
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0828
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22718
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.0462
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          39.00
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     766
_refine_ls_number_reflns         13684
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.2980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                10270
_reflns_number_total             13684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja312125a_si_002.cif
_cod_data_source_block           2814mit
_cod_original_cell_volume        3183.1(6)
_cod_database_code               4119204