Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic Asymmetric Synthesis of γ-Thioesters
Jianwei Sun; Gregory C. Fu; Journal of the American Chemical Society 132 (2010) 4568–4569; doi:10.1021/ja101251d

data_4102225
_publ_section_title
;
 Phosphine-Catalyzed Formation of Carbon-Sulfur Bonds: Catalytic
 Asymmetric Synthesis of \g-Thioesters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4568
_journal_page_last               4569
_journal_paper_doi               10.1021/ja101251d
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H24 O5 S'
_chemical_formula_weight         352.43
_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                 95.9520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6979(2)
_cell_length_b                   5.66190(10)
_cell_length_c                   16.9349(3)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      4.58
_cell_volume                     924.86(3)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_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      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17826
_diffrn_reflns_theta_full        67.73
_diffrn_reflns_theta_max         67.73
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    1.757
_exptl_absorpt_correction_T_max  0.9330
_exptl_absorpt_correction_T_min  0.5053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.265
_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   0.046(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0368P)^2^+0.1825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                3199
_reflns_number_total             3228
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja101251d_si_002.cif
_cod_data_source_block           d09063
_cod_database_code               4102225