Asymmetric Thio-Michael/Nucleophilic Addition Domino Reaction with Chiral N-Sulfinimines
Akio Kamimura; Hidenori Okawa; Yuki Morisaki; Shingo Ishikawa; Hidemitsu Uno; Journal of Organic Chemistry 72 (2007) 3569–3572; doi:10.1021/jo062251h

data_4022723
_publ_section_title
;
 Asymmetric Thio-Michael/Nucleophilic Addition Domino Reaction
 with Chiral N-Sulfinimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3569
_journal_page_last               3572
_journal_paper_doi               10.1021/jo062251h
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C27 H31 N O3 S2 '
_chemical_formula_sum            'C27 H31 N O3 S2'
_chemical_formula_weight         481.67
_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
_audit_creation_date             2006-01-07
_audit_creation_method           'by CrystalStructure 3.7.0'
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.928(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   12.934(7)
_cell_length_b                   5.960(3)
_cell_length_c                   16.380(9)
_cell_measurement_reflns_used    4106
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1258.0(11)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7666
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             512.00
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2159 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5290
_refine_ls_number_restraints     401
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0722P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1349
_reflns_number_gt                4539
_reflns_number_total             5290
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo062251hsi20070307_093903.cif
_cod_data_source_block           '__Sufoximine'
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C27 H31 N O3 S2 '
_cod_database_code               4022723