Direct Catalytic Asymmetric Conjugate Addition of Terminal Alkynes to α,β-Unsaturated Thioamides
Ryo Yazaki; Naoya Kumagai; Masakatsu Shibasaki; Journal of the American Chemical Society 132 (2010) 10275–10277; doi:10.1021/ja105141x

data_4102785
_publ_section_title
;
 Direct Catalytic Asymmetric Conjugate Addition of Terminal Alkynes to
 \a,\b-Unsaturated Thioamides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10275
_journal_page_last               10277
_journal_paper_doi               10.1021/ja105141x
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H19 N S '
_chemical_formula_sum            'C19 H19 N S'
_chemical_formula_weight         293.43
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.852(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   4.8515(2)
_cell_length_b                   10.4926(4)
_cell_length_c                   15.8543(7)
_cell_measurement_reflns_used    6859
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2887
_cell_measurement_theta_min      4.2
_cell_volume                     806.64(6)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.094
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8440
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    1.701
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312.00
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.40
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1297 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2854
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0766P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1993
_reflns_number_gt                1742
_reflns_number_total             2854
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja105141x_si_002.cif
_cod_data_source_block           '_091028-1'
_cod_original_cell_volume        806.63(6)
_cod_original_formula_sum        'C19 H19 N S '
_cod_database_code               4102785