Rhenium-Catalyzed Regio- and Stereoselective Synthesis of γ-Thio-α,β-unsaturated Ketones via Insertion of Terminal Alkynes into the C-S Bond.
Nishi, Mitsumi; Kuninobu, Yoichiro; Takai, Kazuhiko; Organic letters 14 (2012) 6116–6118; doi:10.1021/ol302810u

data_1508765
_publ_section_title
;
 Rhenium-Catalyzed Regio- and Stereoselective Synthesis of
 \g-Thio-\a,\b-unsaturated Ketones via Insertion of Terminal Alkynes into
 the C-S Bond.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6116
_journal_page_last               6118
_journal_paper_doi               10.1021/ol302810u
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C23 H20 O3 S'
_chemical_formula_sum            'C23 H20 O3 S'
_chemical_formula_weight         376.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                94.065(14)
_cell_angle_beta                 97.194(10)
_cell_angle_gamma                90.221(12)
_cell_formula_units_Z            4
_cell_length_a                   9.631(7)
_cell_length_b                   10.862(7)
_cell_length_c                   18.269(12)
_cell_measurement_reflns_used    5854
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.04
_cell_volume                     1891(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1365
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29375
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         2.160
_refine_diff_density_min         -0.660
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     487
_refine_ls_number_reflns         8650
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.1153
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1657P)^2^+1.6597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3099
_reflns_number_gt                6306
_reflns_number_total             8650
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol302810u_si_003.cif
_cod_data_source_block           3a'
_cod_database_code               1508765