Enantioselective synthesis of a GPR40 agonist AMG 837 via catalytic asymmetric conjugate addition of terminal alkyne to α,β-unsaturated thioamide.
Yazaki, Ryo; Kumagai, Naoya; Shibasaki, Masakatsu; Organic letters 13 (2011) 952–955; doi:10.1021/ol102998w

data_1501949
_publ_section_title
;
 Enantioselective synthesis of a GPR40 agonist AMG 837 via catalytic
 asymmetric conjugate addition of terminal alkyne to \a,\b-unsaturated
 thioamide.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              952
_journal_page_last               955
_journal_paper_doi               10.1021/ol102998w
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H25 N O2 S Si'
_chemical_formula_sum            'C18 H25 N O2 S Si'
_chemical_formula_weight         347.55
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.93358(11)
_cell_length_b                   17.3531(4)
_cell_length_c                   18.7692(14)
_cell_measurement_reflns_used    16622
_cell_measurement_temperature    153
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.71
_cell_volume                     1932.59(16)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0.1'
_computing_publication_material  'CrystalStructure 4.0.1 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21992
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.144
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744.00
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.120
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1464 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.006(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     169
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.2896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                3410
_reflns_number_total             3525
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol102998w_si_002.cif
_cod_data_source_block           RY-01
_cod_original_cell_volume        1932.59(15)
_cod_database_code               1501949