Stereocontrolled Fluorobenzylation of Vinyl Sulfones and α,β-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis of Functionalized Enantiomerically Pure Benzylic Fluorides
José Luis García Ruano; José Antonio Fernández-Salas; M. Carmen Maestro; Journal of Organic Chemistry 77 (2012) 2893–2900; doi:10.1021/jo300174k

data_4027081
_publ_section_title
;
 Stereocontrolled Fluorobenzylation of Vinyl Sulfones and
 \a,\b-Unsaturated Esters Mediated by a Remote Sulfinyl Group. Synthesis
 of Functionalized Enantiomerically Pure Benzylic Fluorides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2893
_journal_page_last               2900
_journal_paper_doi               10.1021/jo300174k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C28 H24 F2 O3 S2'
_chemical_formula_weight         510.59
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   5.4880(4)
_cell_length_b                   15.4600(10)
_cell_length_c                   28.8777(17)
_cell_measurement_reflns_used    2091
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.63
_cell_volume                     2450.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0876
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14074
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9496
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      0
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0725P)^2^+0.1196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                3803
_reflns_number_total             4979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300174k_si_001.cif
_cod_data_source_block           carmenmaestro00510_0m
_cod_database_code               4027081