Enantioselective synthesis of imidazolines with quaternary stereocenters by organocatalytic reaction of N-(heteroarenesulfonyl)imines with isocyanoacetates.
Nakamura, Shuichi; Maeno, Yuri; Ohara, Mutsuyo; Yamamura, Akiko; Funahashi, Yasuhiro; Shibata, Norio; Organic letters 14 (2012) 2960–2963; doi:10.1021/ol301256q

data_1507838
_publ_section_title
;
 Enantioselective synthesis of imidazolines with quaternary stereocenters
 by organocatalytic reaction of N-(heteroarenesulfonyl)imines with
 isocyanoacetates.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2960
_journal_page_last               2963
_journal_paper_doi               10.1021/ol301256q
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H26 Br N3 O4 S'
_chemical_formula_sum            'C30 H26 Br N3 O4 S'
_chemical_formula_weight         604.52
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.6985(13)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.2684(9)
_cell_length_b                   15.0353(15)
_cell_length_c                   11.4331(12)
_cell_measurement_reflns_used    4895
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.95
_cell_measurement_theta_min      2.54
_cell_volume                     1380.9(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9274
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.609
_exptl_absorpt_correction_T_max  0.725
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             620.00
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.387
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1293 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.025(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4528
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.033
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0250
_reflns_number_gt                3852
_reflns_number_total             4528
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol301256q_si_001.cif
_cod_data_source_block           imidazoline
_cod_depositor_comments          'Adding full bibliography for 1507838.cif.'
_cod_database_code               1507838