Asymmetric Synthesis of Sulfinamides Using (-)-Quinine as Chiral Auxiliary
Yongda Zhang; Sampada Chitale; Navneet Goyal; Guisheng Li; Zhengxu S. Han; Sherry Shen; Shengli Ma; Nelu Grinberg; Heewon Lee; Bruce Z. Lu; Chris H. Senanayake; Journal of Organic Chemistry 77 (2012) 690–695; doi:10.1021/jo201825b

data_4026833
_publ_section_title
;
 Asymmetric Synthesis of Sulfinamides Using (-)-Quinine as Chiral
 Auxiliary
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              690
_journal_page_last               695
_journal_paper_doi               10.1021/jo201825b
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C29 H34 N2 O3 S'
_chemical_formula_sum            'C29 H34 N2 O3 S'
_chemical_formula_weight         490.64
_chemical_name_common            BI2
_chemical_name_systematic
; 'BI2'
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.502(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.7315(16)
_cell_length_b                   7.0769(9)
_cell_length_c                   13.9820(18)
_cell_measurement_temperature    173(2)
_cell_volume                     1257.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens Platform CCD'
_diffrn_measurement_method       '\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  0.1137
_diffrn_reflns_av_sigmaI/netI    0.1183
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12939
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 2003)'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         4573
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.2054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1483
_reflns_number_gt                3038
_reflns_number_total             4573
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201825b_si_002.cif
_cod_data_source_block           1
_cod_database_code               4026833