Antarafacial Mediation of Oxygen Delivery by a Phenylsulfinyl Group in the Epoxidation of Proximal Double Bonds: Intramolecular Trapping of an Early Pummerer Intermediate with Stereoelectronic Control
Yandong Zhang; Jun Hee Lee; Samuel J. Danishefsky; Journal of the American Chemical Society 133 (2011) 752–755; doi:10.1021/ja1107707

data_4105559
_publ_section_title
;
 Antarafacial Mediation of Oxygen Delivery by a Phenylsulfinyl Group in
 the Epoxidation of Proximal Double Bonds: Intramolecular Trapping of an
 Early Pummerer Intermediate with Stereoelectronic Control
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              752
_journal_page_last               755
_journal_paper_doi               10.1021/ja1107707
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C21 H24 B Cl2 F7 O3 S'
_chemical_formula_weight         571.17
_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                 104.928(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.716(15)
_cell_length_b                   8.052(7)
_cell_length_c                   18.649(16)
_cell_measurement_reflns_used    1159
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      19.34
_cell_measurement_theta_min      2.26
_cell_volume                     2425(4)
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.4835
_diffrn_reflns_av_sigmaI/netI    0.3928
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18185
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.26
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.8501
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.168
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.3357
_refine_ls_R_factor_gt           0.1431
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2854
_refine_ls_wR_factor_ref         0.3614
_reflns_number_gt                1301
_reflns_number_total             4138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1107707_si_003.cif
_cod_data_source_block           ydnws10
_cod_database_code               4105559