Use of Lithiated Chiralo-Sulfinylbenzyl Carbanions for the One-Pot Building of Linear Fragments Containing up to Four Connected Stereocenters
José Luis García Ruano; Esther Torrente; Ana M. Martín-Castro; Journal of Organic Chemistry 78 (2013) 647–657; doi:10.1021/jo3025434

data_4027874
_publ_section_title
;
 Use of Lithiated Chiralo-Sulfinylbenzyl Carbanions for the One-Pot
 Building of Linear Fragments Containing up to Four Connected
 Stereocenters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              647
_journal_page_last               657
_journal_paper_doi               10.1021/jo3025434
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C35 H34 N2 O4 S2'
_chemical_formula_weight         610.76
_chemical_name_systematic
; 
 [1S,1'S,2'S,1''R,(S)S] - N-[1-(2'-{1''-Cyano-1''-[2-(p-tolyl 
sulfinyl)phenyl]ethyl}-5'-oxocyclopentyl)-1-(phenyl)methyl-p-toluenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 98.386(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.156(4)
_cell_length_b                   10.473(2)
_cell_length_c                   16.106(4)
_cell_measurement_reflns_used    4351
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.27
_cell_volume                     3029.8(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0760
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28453
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.13
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      0
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         5915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0688P)^2^+0.3158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                4169
_reflns_number_total             5915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3025434_si_002.cif
_cod_data_source_block           Compound_21a
_cod_original_cell_volume        3029.8(11)
_cod_database_code               4027874