Enantioselective Synthesis of Vinylcyclopropanes and Vinylepoxides Mediated by Camphor-Derived Sulfur Ylides: Rationale of Enantioselectivity, Scope, and Limitation
Xian-Ming Deng; Ping Cai; Song Ye; Xiu-Li Sun; Wei-Wei Liao; Kai Li; Yong Tang; Yun-Dong Wu; Li-Xin Dai; Journal of the American Chemical Society 128 (2006) 9730–9740; doi:10.1021/ja056751o

data_4110745
_publ_section_title
;
 Enantioselective Synthesis of Vinylcyclopropanes and Vinylepoxides
 Mediated by Camphor-Derived Sulfur Ylides: Rationale of
 Enantioselectivity, Scope, and Limitation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9730
_journal_page_last               9740
_journal_paper_doi               10.1021/ja056751o
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H37 Br O2 S Si'
_chemical_formula_weight         425.54
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 94.928(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.444(4)
_cell_length_b                   7.3176(11)
_cell_length_c                   11.7413(18)
_cell_measurement_reflns_used    1618
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.146
_cell_measurement_theta_min      5.763
_cell_volume                     2349.2(6)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    0.1059
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6959
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    1.896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54152
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.772
_exptl_crystal_size_mid          0.339
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.015(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4802
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.804
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                2856
_reflns_number_total             4802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja056751orom20051002_112944.cif
_cod_data_source_block           cd22451
_cod_database_code               4110745