Carbon-Carbon Bond-Forming Reactions of α-Thioaryl Carbonyl Compounds for the Synthesis of Complex Heterocyclic Molecules
James E. Biggs-Houck; Rebecca L. Davis; Jingqiang Wei; Brandon Q. Mercado; Marilyn M. Olmstead; Dean J. Tantillo; Jared T. Shaw; Journal of Organic Chemistry 77 (2012) 160–172; doi:10.1021/jo201541e

data_4026825
_publ_section_title
;
 Carbon-Carbon Bond-Forming Reactions of \a-Thioaryl Carbonyl Compounds
 for the Synthesis of Complex Heterocyclic Molecules
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              160
_journal_page_last               172
_journal_paper_doi               10.1021/jo201541e
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H25 N O4 S'
_chemical_formula_sum            'C26 H25 N O4 S'
_chemical_formula_weight         447.53
_chemical_name_systematic
; 
 (2S,3S)-methyl 1-benzyl-5-oxo-2-phenyl-3-((S)-p-tolylsulfinyl)
 pyrrolidine-3-carboxylate 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 112.147(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.9932(19)
_cell_length_b                   19.5534(18)
_cell_length_c                   12.3256(12)
_cell_measurement_reflns_used    13619
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      1.51
_cell_volume                     4463.0(7)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'Apex 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex DUO'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36153
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9626
_exptl_absorpt_correction_T_min  0.9492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         13619
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.3036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                12669
_reflns_number_total             13619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201541e_si_001_1.cif
_cod_data_source_block           bqm59
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4026825