Chiral Tertiary Amine Thiourea-Catalyzed Asymmetric Inverse-Electron-Demand Diels-Alder Reaction of Chromone Heterodienes Using 3-Vinylindoles as Dienophiles
Zhijie Mao; Aijun Lin; Yan Shi; Haibin Mao; Weipeng Li; Yixiang Cheng; Chengjian Zhu; Journal of Organic Chemistry 78 (2013) 10233–10239; doi:10.1021/jo401592w

data_4028661
_publ_section_title
;
 Chiral Tertiary Amine Thiourea-Catalyzed Asymmetric
 Inverse-Electron-Demand Diels-Alder Reaction of Chromone Heterodienes
 Using 3-Vinylindoles as Dienophiles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10233
_journal_page_last               10239
_journal_paper_doi               10.1021/jo401592w
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_sum            'C25 H23 N O5'
_chemical_formula_weight         417.44
_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                 98.656(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5226(7)
_cell_length_b                   7.2796(6)
_cell_length_c                   14.9337(11)
_cell_measurement_reflns_used    7094
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.89
_cell_measurement_theta_min      5.99
_cell_volume                     1023.42(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7947
_diffrn_reflns_theta_full        65.94
_diffrn_reflns_theta_max         65.94
_diffrn_reflns_theta_min         5.99
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.9062
_exptl_absorpt_correction_T_min  0.8126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.12(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0532P)^2^+0.0904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                2874
_reflns_number_total             2929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401592w_si_001.cif
_cod_data_source_block           cu_20120226aa_0m
_cod_database_code               4028661