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_4114296
_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            'C12 H25 Br Si Te'
_chemical_formula_weight         404.92
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                   11.8162(10)
_cell_length_b                   14.1277(11)
_cell_length_c                   10.3477(8)
_cell_measurement_reflns_used    2403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.611
_cell_measurement_theta_min      4.880
_cell_volume                     1727.4(2)
_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10625
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    4.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65876
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(18)
_refine_ls_extinction_coef       0.00208(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.812
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.812
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.114
_refine_ls_shift/su_mean         0.035
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0139P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                2650
_reflns_number_total             4046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036254csi20030523_101624.cif
_cod_data_source_block           cd23170
_cod_original_formula_sum        'C12 H25  Si Te Br'
_cod_database_code               4114296