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_4102931
_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_formula_moiety         'C14 H13 N O4 '
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.044(14)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.264(5)
_cell_length_b                   8.121(6)
_cell_length_c                   23.197(19)
_cell_measurement_reflns_used    3995
_cell_measurement_temperature    193.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1168.4(16)
_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      193.1
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.974
_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  0.065
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8654
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544.00
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2609
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0008Fo^2^ + 0.1760\s(Fo^2^) + 0.2000]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1412
_reflns_number_gt                1070
_reflns_number_total             2609
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja105048c_si_001_2.cif
_cod_data_source_block           '__2e'
_cod_original_formula_sum        'C14 H13 N O4 '
_cod_database_code               4102931