Enantioselective Synthesis of 2-Substitued-Tetrahydroisoquinolin-1-yl Glycine Derivatives via Oxidative Cross-Dehydrogenative Coupling of Tertiary Amines and Chiral Nickel(II) Glycinate
Shengbin Zhou; Jiang Wang; Daizong Lin; Fei Zhao; Hong Liu; Journal of Organic Chemistry 78 (2013) 11204–11212; doi:10.1021/jo401510b

data_4028741
_publ_section_title
;
 Enantioselective Synthesis of 2-Substitued-Tetrahydroisoquinolin-1-yl
 Glycine Derivatives via Oxidative Cross-Dehydrogenative Coupling of
 Tertiary Amines and Chiral Nickel(II) Glycinate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11204
_journal_page_last               11212
_journal_paper_doi               10.1021/jo401510b
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C42 H38 N4 Ni O3'
_chemical_formula_weight         705.47
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 107.289(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.670(3)
_cell_length_b                   10.967(3)
_cell_length_c                   21.785(6)
_cell_measurement_reflns_used    905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      5.617
_cell_measurement_theta_min      4.605
_cell_volume                     3574.7(16)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1535
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5824
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18737
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.034
_platon_squeeze_details
;
;
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         5824
_refine_ls_number_restraints     353
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1694
_reflns_number_gt                3124
_reflns_number_total             5824
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401510b_si_002.cif
_cod_data_source_block           cd212335
_cod_database_code               4028741