Asymmetric Synthesis of Benzylic Quaternary Difunctionalized Carbons Mediated by a Remote Sulfinyl Group
José Luis García Ruano; Esther Torrente; Ana M. Martín-Castro; Journal of Organic Chemistry 76 (2011) 3597–3603; doi:10.1021/jo2004204

data_4026272
_publ_section_title
;
 Asymmetric Synthesis of Benzylic Quaternary Difunctionalized Carbons
 Mediated by a Remote Sulfinyl Group
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3597
_journal_page_last               3603
_journal_paper_doi               10.1021/jo2004204
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C18 H17 N O2 S'
_chemical_formula_weight         311.39
_chemical_name_systematic
; 
[2R,(S)S]-2-Methyl-3-oxo-2-[2-(p-tolylsulfinyl)phenyl]butanenitrile
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.0786(2)
_cell_length_b                   8.0786(2)
_cell_length_c                   48.3211(9)
_cell_measurement_temperature    100(2)
_cell_volume                     3153.62(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 0.978
_diffrn_measured_fraction_theta_max 0.979
_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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            10948
_diffrn_reflns_theta_full        69.36
_diffrn_reflns_theta_max         69.36
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      0
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0536P)^2^+0.0160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                2569
_reflns_number_total             2770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2004204_si_001.cif
_cod_data_source_block           Compound_4A
_cod_database_code               4026272