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_4022724
_publ_contact_author_email       uno@dpc.ehime-u.ac.jp
_publ_contact_author_fax         +81-89-927-9670
_publ_contact_author_name        'Prof Hidemitsu Uno'
_publ_contact_author_phone       +81-89-927-9660
_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 rmad
_chemical_formula_moiety         'C24 H33 N O3 S2 '
_chemical_formula_sum            'C24 H33 N O3 S2'
_chemical_formula_weight         447.65
_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             2007-03-07
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.408(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.090(6)
_cell_length_b                   8.726(5)
_cell_length_c                   14.035(9)
_cell_measurement_reflns_used    5466
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1234.6(13)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8.1'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 14.6199
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Mercury-8 (2x2 bin mode)'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24229
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(9)
_refine_ls_extinction_coef       0.059(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5525
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0932P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1791
_reflns_number_gt                3897
_reflns_number_total             5525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062251hsi20070307_093920.cif
_cod_data_source_block           '__AKiPr'
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C24 H33 N O3 S2 '
_cod_database_code               4022724