Enantioselective Halocyclization Using Reagents Tailored for Chiral Anion Phase-Transfer Catalysis
Yi-Ming Wang; Jeffrey Wu; Christina Hoong; Vivek Rauniyar; F. Dean Toste; Journal of the American Chemical Society 134 (2012) 12928–12931; doi:10.1021/ja305795x

data_4118491
_publ_section_title
;
 Enantioselective Halocyclization Using Reagents Tailored for Chiral Anion
 Phase-Transfer Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12928
_journal_page_last               12931
_journal_paper_doi               10.1021/ja305795x
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C39 H67 B3 Br F12 N7 O6'
_chemical_formula_weight         1070.34
_chemical_name_common            Selectbro
_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                 90.0810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.3479(11)
_cell_length_b                   14.1583(8)
_cell_length_c                   17.4224(10)
_cell_measurement_reflns_used    9382
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.54
_cell_volume                     5019.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR-2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega 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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            80923
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.8676
_exptl_absorpt_correction_T_min  0.7840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         2.883
_refine_diff_density_min         -1.537
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         9175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0713
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0936P)^2^+19.4834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.1892
_reflns_number_gt                8309
_reflns_number_total             9175
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305795x_si_004.cif
_cod_data_source_block           shelxl
_cod_database_code               4118491