Asymmetric [2,3]-Wittig rearrangement induced by a chiral carbanion whose chirality was transferred from an epoxide.
Sasaki, Michiko; Higashi, Mariko; Masu, Hyuma; Yamaguchi, Kentaro; Takeda, Kei; Organic letters 7 (2005) 5913–5915; doi:10.1021/ol052544h

data_1506778
_publ_section_title
;
 Asymmetric [2,3]-Wittig rearrangement induced by a chiral carbanion whose
 chirality was transferred from an epoxide.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              5913
_journal_page_last               5915
_journal_paper_doi               10.1021/ol052544h
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C28 H31 Br O3 Si'
_chemical_formula_weight         523.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 105.942(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.718(3)
_cell_length_b                   6.6546(6)
_cell_length_c                   26.833(3)
_cell_measurement_reflns_used    1975
_cell_measurement_temperature    150
_cell_measurement_theta_max      20.4835
_cell_measurement_theta_min      2.3645
_cell_volume                     5274.1(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Smart1000 CCD'
_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  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15087
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    1.630
_exptl_absorpt_correction_T_max  0.9229
_exptl_absorpt_correction_T_min  0.4961
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.173
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+15.4143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.2080
_reflns_number_gt                3118
_reflns_number_total             5978
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052544hsi20051020_062541.cif
_cod_data_source_block           5026mas
_cod_original_cell_volume        5274.0(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1506778