Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary N-Hydroxyindolines
Yang, Yu; Ren, Hong-Xia; Chen, Feng; Zhang, Zheng-Bing; Zou, Ying; Chen, Chao; Song, Xiang-Jia; Tian, Fang; Peng, Lin; Wang, Li-Xin; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b00893

data_1546022
_publ_section_title
;
 Organocatalytic Asymmetric Annulation between Hydroxymaleimides and
 Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary
 N-Hydroxyindolines
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b00893
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H15 Br N2 O4'
_chemical_formula_weight         403.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 107.727(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.578(3)
_cell_length_b                   22.365(5)
_cell_length_c                   12.644(3)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.49
_cell_volume                     3388.0(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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32876
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.173
_diffrn_reflns_theta_min         0.910
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_T_max  0.20880
_exptl_absorpt_correction_T_min  0.11770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.500
_refine_diff_density_max         2.061
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details
;
 Flack x determined using 5602 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.047(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     912
_refine_ls_number_reflns         16635
_refine_ls_number_restraints     965
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+5.3028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                14474
_reflns_number_total             16635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00893_si_001.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        3387.9(12)
_cod_database_code               1546022
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.299
_shelx_estimated_absorpt_t_max   0.374
_shelx_res_checksum              88269
_shelx_hkl_checksum              31175