Optical Resolution of (\±)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine as a Chiral Framework for 2-Iminoimidazolidine with 2-Methylphenyl Pendant and the Guanidine-Catalyzed Asymmetric Michael Reaction of tert-Butyl Diphenyliminoacetate and Ethyl Acrylate
Akemi Ryoda; Nana Yajima; Toyokazu Haga; Takuya Kumamoto; Waka Nakanishi; Masatoshi Kawahata; Kentaro Yamaguchi; Tsutomu Ishikawa; Journal of Organic Chemistry 73 (2008) 133–141; doi:10.1021/jo701923z

data_4023170
_publ_contact_author_address
;Graduate School of Pharmaceutical Sciences
Chiba University
1-33 Yayoi-cho
Inage-ku
Chiba-shi
Chiba 263-8522
Japan
;
_publ_contact_author_email       benti@p.chiba-u.ac.jp
_publ_contact_author_fax         81(43)2902910
_publ_contact_author_name        'Professor Tsutomu Ishikawa'
_publ_contact_author_phone       81(43)2902910
_publ_section_title
;
 Optical Resolution of (\+-)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine
 as a Chiral Framework for 2-Iminoimidazolidine with 2-Methylphenyl
 Pendant and the Guanidine-Catalyzed Asymmetric Michael Reaction
 of tert-Butyl Diphenyliminoacetate and Ethyl Acrylate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              133
_journal_page_last               141
_journal_paper_doi               10.1021/jo701923z
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '2(C16 H16 N2), 4(C10 H15 O4 S), 5(C6 H6)'
_chemical_formula_sum            'C102 H134 N4 O16 S4'
_chemical_formula_weight         1800.37
_chemical_name_common            'Tri(1S)-(+)-10-CSA Salt'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.818(4)
_cell_angle_beta                 99.498(4)
_cell_angle_gamma                114.094(2)
_cell_formula_units_Z            1
_cell_length_a                   13.038(3)
_cell_length_b                   14.627(3)
_cell_length_c                   16.662(6)
_cell_measurement_reflns_used    5736
_cell_measurement_temperature    90
_cell_measurement_theta_max      21.89
_cell_measurement_theta_min      2.18
_cell_volume                     2649.2(13)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19659
_diffrn_reflns_theta_full        22.22
_diffrn_reflns_theta_max         22.22
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9423
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             966
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
;
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1147
_refine_ls_number_reflns         13233
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0677P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                11194
_reflns_number_total             13233
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo701923z-File001.cif
_cod_data_source_block           AR02112A
_cod_database_code               4023170