Tandem Michael Addition/Ylide Epoxidation for the Synthesis of Highly Functionalized Cyclohexadiene Epoxide Derivatives
Qing-Gang Wang; Xian-Ming Deng; Ben-Hu Zhu; Long-Wu Ye; Xiu-Li Sun; Chuan-Ying Li; Chun-Yin Zhu; Qi Shen; Yong Tang; Journal of the American Chemical Society 130 (2008) 5408–5409; doi:10.1021/ja800747m

data_4107715
_publ_section_title
;
 Tandem Michael Addition/Ylide Epoxidation for the Synthesis of Highly
 Functionalized Cyclohexadiene Epoxide Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5408
_journal_page_last               5409
_journal_paper_doi               10.1021/ja800747m
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H19 Br O2'
_chemical_formula_weight         359.25
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 93.604(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2797(15)
_cell_length_b                   24.896(6)
_cell_length_c                   10.252(2)
_cell_measurement_reflns_used    1642
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.304
_cell_measurement_theta_min      5.154
_cell_volume                     1599.6(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1099
_diffrn_reflns_av_sigmaI/netI    0.0716
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4652
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    2.574
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7560
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.136
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1120P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1785
_reflns_number_gt                1969
_reflns_number_total             2785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja800747m-file003.cif
_cod_data_source_block           cd2764
_cod_database_code               4107715