Highly efficient enantioselective three-component synthesis of 2-amino-4H-chromenes catalysed by chiral tertiary amine-thioureas
Gaosheng; Yang; Yang Gaosheng; Chongrong Luo; Xiaolong Mu; Tingting Wang; Xin-Yuan Liu; Chem.Commun. 48 (2012) 5880–; doi:10.1039/c2cc30731f

data_7107795
_publ_section_title
;
 Highly efficient enantioselective three-component synthesis of
 2-amino-4H-chromenes catalysed by chiral tertiary amine-thioureas
;
_journal_name_full               Chem.Commun.
_journal_page_first              5880
_journal_paper_doi               10.1039/c2cc30731f
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration S
_chemical_formula_sum            'C13 H13 Br N2 O5'
_chemical_formula_weight         357.16
_chemical_name_systematic
;
Ethyl 2-amino-6-bromo-4-(nitromethyl)-4H-chromene-3-carboxylate
;
_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                 96.083(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.413(2)
_cell_length_b                   17.675(7)
_cell_length_c                   7.539(3)
_cell_measurement_temperature    293(2)
_cell_volume                     717.2(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5934
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    2.889
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.603497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.076
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0954P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                2249
_reflns_number_total             2951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc30731f.txt
_cod_data_source_block           110321b
_cod_original_cell_volume        717.3(5)
_cod_original_sg_symbol_H-M      'P2(1) '
_cod_database_code               7107795