Controllable Diastereoselective Cyclopropanation. Enantioselective Synthesis of Vinylcyclopropanes via Chiral Telluronium Ylides
Wei-Wei Liao; Kai Li; Yong Tang; Journal of the American Chemical Society 125 (2003) 13030–13031; doi:10.1021/ja036254c

data_4114297
_publ_section_title
;
 Controllable Diastereoselective Cyclopropanation. Enantioselective
 Synthesis of Vinylcyclopropanes via Chiral Telluronium Ylides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13030
_journal_page_last               13031
_journal_paper_doi               10.1021/ja036254c
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C21 H23 Br O Si'
_chemical_formula_weight         399.39
_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                   6.1465(5)
_cell_length_b                   16.5995(14)
_cell_length_c                   19.9580(16)
_cell_measurement_reflns_used    2422
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.038
_cell_measurement_theta_min      4.763
_cell_volume                     2036.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12465
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    2.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48390
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.746
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4701
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.747
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0178P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0612
_reflns_number_gt                2439
_reflns_number_total             4701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036254csi20030523_101649.cif
_cod_data_source_block           cd23130
_cod_database_code               4114297