A Dramatic Switch of Enantioselectivity in Asymmetric Heck Reaction by Benzylic Substituents of Ligands
Wen-Qiong Wu; Qian Peng; Da-Xuan Dong; Xue-Long Hou; Yun-Dong Wu; Journal of the American Chemical Society 130 (2008) 9717–9725; doi:10.1021/ja7104174

data_4108095
_publ_section_title
;
 A Dramatic Switch of Enantioselectivity in Asymmetric Heck Reaction by
 Benzylic Substituents of Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9717
_journal_page_last               9725
_journal_paper_doi               10.1021/ja7104174
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H27 Cl2 N O1.5 P Pd'
_chemical_formula_weight         573.75
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0957(6)
_cell_length_b                   14.0633(8)
_cell_length_c                   19.3858(11)
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.350
_cell_measurement_theta_min      5.104
_cell_volume                     2752.4(3)
_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 0.994
_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  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16714
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77014
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6247
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.170
_refine_ls_shift/su_mean         0.149
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                5047
_reflns_number_total             6247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7104174-file004.cif
_cod_data_source_block           cd26507
_cod_original_formula_sum        'C25 H27 Cl2 N O1.50 P Pd'
_cod_database_code               4108095