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_4027876
_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            'C22 H23 N O3 S'
_chemical_formula_weight         381.47
_chemical_name_systematic
; 
 (2R,1'S,2'R)-2-(2'-Methyl-3'-oxocyclopentyl)-2-[2-(p-tolylsulfonyl)-
phenyl]propanenitrile 
;
_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                 98.680(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7205(4)
_cell_length_b                   8.3352(3)
_cell_length_c                   26.3932(10)
_cell_measurement_temperature    100(2)
_cell_volume                     1896.47(13)
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15774
_diffrn_reflns_theta_full        71.94
_diffrn_reflns_theta_max         71.94
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    1.697
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      0
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.917
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.060(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         6680
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0772P)^2^+0.8061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                6392
_reflns_number_total             6680
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3025434_si_004.cif
_cod_data_source_block           Compound_23a
_cod_database_code               4027876