Direct Asymmetric Synthesis of β-Bis-Aryl-α-Amino Acid Esters via Enantioselective Copper-Catalyzed Addition ofp-Quinone Methides
He, Fu-Sheng; Jin, Jing-Hai; Yang, Zhong-Tao; Yu, Xingxin; Fossey, John S.; Deng, Wei-Ping; ACS Catalysis 6 (2016) 652–; doi:10.1021/acscatal.5b02619

data_4513757
_publ_section_title
;
 Direct Asymmetric Synthesis of \b-Bis-Aryl-\a-Amino Acid Esters via
 Enantioselective Copper-Catalyzed Addition ofp-Quinone Methides
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              652
_journal_paper_doi               10.1021/acscatal.5b02619
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C37 H40 Br N O3'
_chemical_formula_weight         626.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.038(2)
_cell_length_b                   15.921(3)
_cell_length_c                   20.131(4)
_cell_measurement_reflns_used    3323
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      43.269
_cell_measurement_theta_min      4.534
_cell_volume                     3217.2(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22357
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.631
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 1830 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5990
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0349P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4904
_reflns_number_total             5990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b02619_si_002.cif
_cod_data_source_block           mo_dm15406_0m
_cod_depositor_comments          'Adding full bibliography for 4513757.cif.'
_cod_original_cell_volume        3217.3(12)
_cod_database_code               4513757
_shelx_estimated_absorpt_t_min   0.789
_shelx_estimated_absorpt_t_max   0.867
_shelxl_version_number           2013-4
_shelx_res_checksum              21669
_shelx_hkl_checksum              22368