Enantioselective synthesis of 3-amino-hydrobenzofuran-2,5-diones via Cu(i)-catalyzed intramolecular conjugate addition of imino esters
Yang, Wu-Lin; Sun, Zhong-Tao; Zhang, Jian; Li, Zhong; Deng, Wei-Ping; Organic Chemistry Frontiers 6 (2019) 579–; doi:10.1039/C8QO01335G

data_1554573
_publ_section_title
;
 Enantioselective synthesis of 3-amino-hydrobenzofuran-2,5-diones via
 Cu(i)-catalyzed intramolecular conjugate addition of imino esters
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              579
_journal_paper_doi               10.1039/C8QO01335G
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-12-06 deposited with the CCDC.
2019-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                84.194(6)
_cell_angle_beta                 79.023(6)
_cell_angle_gamma                64.094(6)
_cell_formula_units_Z            2
_cell_length_a                   6.9308(8)
_cell_length_b                   6.9507(8)
_cell_length_c                   11.8464(14)
_cell_measurement_reflns_used    6254
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      139.890
_cell_measurement_theta_min      7.603
_cell_volume                     503.84(11)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12059
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.153
_diffrn_reflns_theta_min         3.802
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.24(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.0358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                3148
_reflns_number_total             3664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01335g2.cif
_cod_data_source_block           cu_d8v18549_0m
_cod_original_cell_volume        503.84(10)
_cod_database_code               1554573
_shelx_estimated_absorpt_t_min   0.884
_shelx_estimated_absorpt_t_max   0.939
_shelxl_version_number           2013-4
_shelx_res_checksum              58279
_shelx_hkl_checksum              35841