Gold(I)-Catalyzed Enantioselective Synthesis of Benzopyrans via Rearrangement of Allylic Oxonium Intermediates
Minoru Uemura; Iain D. G. Watson; Mikimoto Katsukawa; F. Dean Toste; Journal of the American Chemical Society 131 (2009) 3464–3465; doi:10.1021/ja900155x

data_4104035
_publ_section_title
;
 Gold(I)-Catalyzed Enantioselective Synthesis of Benzopyrans via
 Rearrangement of Allylic Oxonium Intermediates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3464
_journal_page_last               3465
_journal_paper_doi               10.1021/ja900155x
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 Br O3'
_chemical_formula_sum            'C24 H25 Br O3'
_chemical_formula_weight         441.35
_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                   6.5984(11)
_cell_length_b                   12.125(2)
_cell_length_c                   26.515(5)
_cell_measurement_reflns_used    5407
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.9
_cell_volume                     2121.3(6)
_computing_cell_refinement       'Bruker APEX2 v.2008.6-1'
_computing_data_collection       'Bruker APEX2 v.2008.6-1'
_computing_data_reduction        'SAINT v. 7.60A'
_computing_molecular_graphics    'Bruker-AXS, XP v.6'
_computing_publication_material  'Bruker-AXS, XP v.6'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       '\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  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14031
_diffrn_reflns_theta_full        25.46
_diffrn_reflns_theta_max         25.46
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1603 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.005(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                3025
_reflns_number_total             3890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja900155x_si_002.cif
_cod_data_source_block           minbrs
_cod_database_code               4104035