A Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and Functionalization
Chaosheng Luo; Yong Huang; Journal of the American Chemical Society 135 (2013) 8193–8196; doi:10.1021/ja4040945

data_4119875
_publ_section_title
;
 A Highly Diastereo- and Enantioselective Synthesis of
 Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and
 Functionalization
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8193
_journal_page_last               8196
_journal_paper_doi               10.1021/ja4040945
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 Br2 N2 O4'
_chemical_formula_sum            'C20 H20 Br2 N2 O4'
_chemical_formula_weight         512.20
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 112.876(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1217(4)
_cell_length_b                   8.7843(4)
_cell_length_c                   11.5453(8)
_cell_measurement_reflns_used    4877
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      68.10
_cell_measurement_theta_min      6.50
_cell_volume                     1039.22(11)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6859
_diffrn_reflns_theta_full        68.09
_diffrn_reflns_theta_max         68.09
_diffrn_reflns_theta_min         6.54
_exptl_absorpt_coefficient_mu    5.191
_exptl_absorpt_correction_T_max  0.4233
_exptl_absorpt_correction_T_min  0.3050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0093P)^2^+2.1398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                3176
_reflns_number_total             3390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4040945_37.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1039.22(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4119875