Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration.
Yang, Yang; Perry, Ian B.; Buchwald, Stephen L.; Journal of the American Chemical Society 138 (2016) 9787–9790; doi:10.1021/jacs.6b06299

data_4130741
_publ_section_title
;
 Copper-Catalyzed Enantioselective Addition of Styrene-Derived
 Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective
 Hydrocupration.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9787
_journal_page_last               9790
_journal_paper_doi               10.1021/jacs.6b06299
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H25 Br N O P'
_chemical_formula_weight         490.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 107.031(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3219(15)
_cell_length_b                   9.9416(12)
_cell_length_c                   20.196(3)
_cell_measurement_reflns_used    9491
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.68
_cell_volume                     2365.5(5)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13239
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         1.728
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    1.824
_exptl_absorpt_correction_T_max  0.265674
_exptl_absorpt_correction_T_min  0.181028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         1.579
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
; 
 Flack x determined using 5230 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.020(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         13239
_refine_ls_number_restraints     897
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+0.2056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                12103
_reflns_number_total             13239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b06299_si_005.cif
_cod_data_source_block           X16029_t4
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4130741
_shelx_estimated_absorpt_t_min   0.487
_shelx_estimated_absorpt_t_max   0.853
_shelxl_version_number           2014/6
_shelx_res_checksum              90184
_shelx_hkl_checksum              77402