Design of N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromides as Novel Chiral Phase-Transfer Catalysts: Synthesis and Application to Practical Asymmetric Synthesis of α-Amino Acids
Takashi Ooi; Minoru Kameda; Keiji Maruoka; Journal of the American Chemical Society 125 (2003) 5139–5151; doi:10.1021/ja021244h

data_4113679
_publ_contact_author_address
;
    Dept.of Chem., Grad.School of Sci., Kyoto Univ., Kyoto 606-8502 JAPAN
;
_publ_contact_author_email       ' maruoka@kuchem.kyoto-u.ac.jp '
_publ_contact_author_fax         ' +81-(0)75-753-4041 '
_publ_contact_author_name        ' Keiji Maruoka (MS #JA021244H) '
_publ_contact_author_phone       ' +81-(0)75-753-4041 '
_publ_section_title
;
 Design of N-Spiro C2-Symmetric Chiral Quaternary Ammonium Bromides as
 Novel Chiral Phase-Transfer Catalysts: Synthesis and Application to
 Practical Asymmetric Synthesis of \a-Amino Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5139
_journal_page_last               5151
_journal_paper_doi               10.1021/ja021244h
_journal_volume                  125
_journal_year                    2003
_chemical_absolute_configuration rm
_chemical_formula_sum            'C50 H44 Br N3'
_chemical_formula_weight         766.82
_space_group_IT_number           24
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      24
_symmetry_space_group_name_Hall  'I 2b 2c'
_symmetry_space_group_name_H-M   'I 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6723(9)
_cell_length_b                   25.127(1)
_cell_length_c                   10.8390(5)
_cell_measurement_temperature    288.2
_cell_volume                     3996.0(3)
_computing_cell_refinement       PROCESS
_computing_data_collection       PROCESS
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9937
_diffrn_measured_fraction_theta_max 0.9937
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4311
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourlessprism
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.13
_refine_diff_density_min         -0.76
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2543
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.0193
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.08000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2064
_reflns_number_gt                1386
_reflns_number_total             2543
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja021244h_2.cif
_cod_data_source_block           kameda5
_cod_original_cell_volume        3996.1(4)
_cod_original_sg_symbol_H-M      'I 21 21 21 '
_cod_original_formula_sum        'C50 H44 Br N3 '
_cod_database_code               4113679