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_4105561
_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_absolute_configuration unk
_chemical_formula_sum            'C21 H28 O2 S'
_chemical_formula_weight         344.49
_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                   5.9163(11)
_cell_length_b                   11.863(2)
_cell_length_c                   26.721(5)
_cell_measurement_reflns_used    8386
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.26
_cell_measurement_theta_min      2.30
_cell_volume                     1875.4(6)
_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  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            30247
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9175
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.47(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         5744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0429P)^2^+0.0594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                4419
_reflns_number_total             5744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1107707_si_005.cif
_cod_data_source_block           yd4s10
_cod_database_code               4105561