Highly regio-, diastereo- and enantioselective one-pot gold/chiral Brønsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines.
Liu, Xin-Yuan; Xiao, Ya-Ping; Siu, Fung-Ming; Ni, Li-Chen; Chen, Yong; Wang, Lin; Che, Chi-Ming; Organic & biomolecular chemistry 10 (2012) 7208–7219; doi:10.1039/c2ob25753j

data_7152547
_publ_section_title
;
 Highly regio-, diastereo- and enantioselective one-pot gold/chiral
 Br\/onsted acid-catalysed cascade synthesis of bioactive diversely
 substituted tetrahydroquinolines.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7208
_journal_page_last               7219
_journal_paper_doi               10.1039/c2ob25753j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C22 H20 Br N O'
_chemical_formula_weight         394.30
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7061(5)
_cell_length_b                   17.0480(15)
_cell_length_c                   18.4614(16)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      85
_cell_measurement_theta_min      5
_cell_volume                     1795.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10032
_diffrn_reflns_theta_full        65.94
_diffrn_reflns_theta_max         65.94
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    3.178
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.5036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0640
_reflns_number_gt                2936
_reflns_number_total             2984
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25753j.txt
_cod_data_source_block           cheny21
_cod_database_code               7152547