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_4110742
_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            'C22 H23 Cl O'
_chemical_formula_weight         338.85
_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                   5.7455(9)
_cell_length_b                   16.488(3)
_cell_length_c                   20.354(3)
_cell_measurement_reflns_used    1161
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.461
_cell_measurement_theta_min      4.703
_cell_volume                     1928.2(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0809
_diffrn_reflns_av_sigmaI/netI    0.0999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11715
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65157
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.499
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0397P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                2151
_reflns_number_total             4374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja056751orom20051002_112851.cif
_cod_data_source_block           cd23372
_cod_database_code               4110742