Highly Enantioselective Hydrogenative Desymmetrization of Bicyclic Imides Leading to Multiply Functionalized Chiral Cyclic Compounds
Masato Ito; Chika Kobayashi; Akio Himizu; Takao Ikariya; Journal of the American Chemical Society 132 (2010) 11414–11415; doi:10.1021/ja105048c

data_4102930
_publ_contact_author_address
;
    Institute of Materials Chemistry and Engineering
    Kyushu University
    6-1 Kasuga-koen, Kasuga city, Fukuoka 816-8580, Japan
;
_publ_contact_author_email       mito@cm.kyushu-u.ac.jp
_publ_contact_author_fax         81(92)5837810
_publ_contact_author_name        'Masato ITO'
_publ_contact_author_phone       81(92)5837808
_publ_section_title
;
 Highly Enantioselective Hydrogenative Desymmetrization of Bicyclic Imides
 Leading to Multiply Functionalized Chiral Cyclic Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11414
_journal_page_last               11415
_journal_paper_doi               10.1021/ja105048c
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H18 Br N O3 '
_chemical_formula_sum            'C15 H18 Br N O3'
_chemical_formula_weight         340.22
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.057(4)
_cell_length_b                   6.437(6)
_cell_length_c                   43.83(4)
_cell_measurement_reflns_used    3044
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     1427(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            13758
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    2.896
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_correction_T_min  0.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.63
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1250 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.006(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3189
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0005Fo^2^ + 0.1500\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                2748
_reflns_number_total             3189
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja105048c_si_001_1.cif
_cod_data_source_block           '__4g'
_cod_original_formula_sum        'C15 H18 Br N O3 '
_cod_database_code               4102930