Enantioselective Preparation of 8-Oxabicyclo[3.2.1]octane Derivatives via Asymmetric [3+2]-Cycloaddition of Platinum-Containing Carbonyl Ylides with Vinyl Ethers
Kento Ishida; Hiroyuki Kusama; Nobuharu Iwasawa; Journal of the American Chemical Society 132 (2010) 8842–8843; doi:10.1021/ja102391t

data_4102618
_publ_section_title
;
 Enantioselective Preparation of 8-Oxabicyclo[3.2.1]octane Derivatives via
 Asymmetric [3+2]-Cycloaddition of Platinum-Containing Carbonyl Ylides
 with Vinyl Ethers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8842
_journal_page_last               8843
_journal_paper_doi               10.1021/ja102391t
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C21 H22 Br2 O2'
_chemical_formula_sum            'C21 H22 Br2 O2'
_chemical_formula_weight         466.21
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 98.649(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1406(3)
_cell_length_b                   24.5387(11)
_cell_length_c                   11.2924(6)
_cell_measurement_reflns_used    18923
_cell_measurement_temperature    171(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.00
_cell_volume                     1956.16(16)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-2004 (Burla, 2005)'
_diffrn_ambient_temperature      171(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP Area Detector System'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18923
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.155
_exptl_absorpt_correction_T_max  0.4904
_exptl_absorpt_correction_T_min  0.3687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.728
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         8807
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.728
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0357
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                7482
_reflns_number_total             8807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja102391t_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1956.14(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4102618