Enantioselective, Palladium-Catalyzed Conjugate Additions of Arylboronic Acids to Form Bis-benzylic Quaternary Stereocenters.
Kadam, Abhishek A.; Ellern, Arkady; Stanley, Levi M.; Organic letters 19 (2017) 4062–4065; doi:10.1021/acs.orglett.7b01825

data_1547125
_publ_section_title
;
 Enantioselective, Palladium-Catalyzed Conjugate Additions of Arylboronic
 Acids to Form Bis-benzylic Quaternary Stereocenters.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4062
_journal_page_last               4065
_journal_paper_doi               10.1021/acs.orglett.7b01825
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration S
_chemical_formula_moiety         'C26 H26 N4 O5'
_chemical_formula_sum            'C26 H26 N4 O5'
_chemical_formula_weight         474.51
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                81.103(9)
_cell_angle_beta                 84.522(12)
_cell_angle_gamma                84.478(11)
_cell_formula_units_Z            2
_cell_length_a                   7.2089(18)
_cell_length_b                   8.081(2)
_cell_length_c                   20.594(6)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      59.7725
_cell_measurement_theta_min      2.1774
_cell_volume                     1175.8(5)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 Suite (Bruker AXS, 2016)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2016)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX3 Suite (Bruker AXS, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method
' calculated 99% coverage BRUKER QUINN strategy'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'CuK\a '
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27795
_diffrn_reflns_theta_full        60.16
_diffrn_reflns_theta_max         60.16
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'X-ray tuve'
_diffrn_source_type              'Sealed tube'
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.173
_refine_ls_abs_structure_details
;
 Flack x determined using 2726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

For this structure Parson parameter 0.08(8), Hooft 0.07(7)
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     644
_refine_ls_number_reflns         6724
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.1699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                6065
_reflns_number_total             6724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01825_si_002.cif
_cod_data_source_block           Sta015
_cod_original_cell_volume        1175.8(6)
_cod_database_code               1547125
_shelx_res_checksum              5844
_shelx_hkl_checksum              61231