Asymmetric Michael Addition of α-Substituted Isocyanoacetates with Maleimides Catalyzed by Chiral Tertiary Amine Thiourea
Jian-Fei Bai; Liang-Liang Wang; Lin Peng; Yun-Long Guo; Li-Na Jia; Fang Tian; Guang-Yun He; Xiao-Ying Xu; Li-Xin Wang; Journal of Organic Chemistry 77 (2012) 2947–2953; doi:10.1021/jo2025288

data_4027066
_publ_section_title
;
 Asymmetric Michael Addition of \a-Substituted Isocyanoacetates with
 Maleimides Catalyzed by Chiral Tertiary Amine Thiourea
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2947
_journal_page_last               2953
_journal_paper_doi               10.1021/jo2025288
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 Br N2 O4'
_chemical_formula_sum            'C21 H17 Br N2 O4'
_chemical_formula_weight         441.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   6.611(3)
_cell_length_b                   14.222(6)
_cell_length_c                   20.570(9)
_cell_measurement_reflns_used    6318
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.44
_cell_volume                     1934.0(15)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.1122
_diffrn_reflns_av_sigmaI/netI    0.1032
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15446
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    2.155
_exptl_absorpt_correction_T_max  0.6976
_exptl_absorpt_correction_T_min  0.3138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.809
_refine_diff_density_min         -2.602
_refine_diff_density_rms         0.255
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.1430
_refine_ls_R_factor_gt           0.0952
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1034P)^2^+28.7936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2499
_refine_ls_wR_factor_ref         0.2790
_reflns_number_gt                3475
_reflns_number_total             4661
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2025288_si_001.cif
_cod_data_source_block           mo_wb_wlx_1_sad
_cod_database_code               4027066