Facile construction of three contiguous stereogenic centers via dynamic kinetic resolution in asymmetric transfer hydrogenation of quinolines
Mu-Wang Chen; Xian-Feng Cai; Zhang-Pei Chen; Lei Shi; Yong-Gui Zhou; Chem.Commun. 50 (2014) 12526–; doi:10.1039/C4cc06060A

data_7115765
_publ_section_title
;
 Facile construction of three contiguous stereogenic centers via dynamic
 kinetic resolution in asymmetric transfer hydrogenation of quinolines
;
_journal_name_full               Chem.Commun.
_journal_page_first              12526
_journal_paper_doi               10.1039/C4cc06060A
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H24 Br N O'
_chemical_formula_weight         398.33
_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                 97.490(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.705(2)
_cell_length_b                   9.823(3)
_cell_length_c                   11.361(3)
_cell_measurement_reflns_used    1230
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.923
_cell_measurement_theta_min      4.719
_cell_volume                     963.2(4)
_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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5846
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    2.143
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13408
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0340P)^2^+0.0276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                2064
_reflns_number_total             2849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06060a2.cif
_cod_data_source_block           cd212185
_cod_original_cell_volume        963.3(5)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7115765