A Highly Stereoselective Addition of Lithiated Ynamides to Ellman–Davis ChiralN-tert-Butanesulfinyl Imines
Wang, Xiao-Na; Hsung, Richard P.; Qi, Rui; Fox, Sierra K.; Lv, Ming-Can; Organic Letters 15 (2013) 2514–; doi:10.1021/ol400989x

data_1512076
_publ_section_title
;
 A Highly Stereoselective Addition of Lithiated Ynamides to Ellman--Davis
 ChiralN-tert-Butanesulfinyl Imines
;
_journal_issue                   10
_journal_name_full               'Organic Letters'
_journal_page_first              2514
_journal_paper_doi               10.1021/ol400989x
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration adrm
_chemical_formula_moiety         'C16 H20 N2 O3 S'
_chemical_formula_sum            'C16 H20 N2 O3 S'
_chemical_formula_weight         320.40
_chemical_name_common            13013a
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9941(7)
_cell_length_b                   15.9821(19)
_cell_length_c                   16.971(2)
_cell_measurement_reflns_used    2806
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      2.55
_cell_volume                     1625.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17149
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008/1)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3696
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0416P)^2^+0.3261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                3091
_reflns_number_total             3696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400989x_si_004.cif
_cod_data_source_block           13013a
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1512076