Desymmetrization of Cyclohexadienones via Brønsted Acid-Catalyzed Enantioselective Oxo-Michael Reaction
Qing Gu; Zi-Qiang Rong; Chao Zheng; Shu-Li You; Journal of the American Chemical Society 132 (2010) 4056–4057; doi:10.1021/ja100207s

data_4102153
_publ_section_title
;
 Desymmetrization of Cyclohexadienones via Br\/onsted Acid-Catalyzed
 Enantioselective Oxo-Michael Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4056
_journal_page_last               4057
_journal_paper_doi               10.1021/ja100207s
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H13 Br O3'
_chemical_formula_weight         309.15
_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                   6.2423(9)
_cell_length_b                   8.3280(13)
_cell_length_c                   25.041(4)
_cell_measurement_reflns_used    2225
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.460
_cell_measurement_theta_min      5.155
_cell_volume                     1301.8(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0969
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7138
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    3.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75271
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(13)
_refine_ls_extinction_coef       0.0268(19)
_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   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0421P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                1858
_reflns_number_total             2564
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja100207s_si_002.cif
_cod_data_source_block           cd29422
_cod_database_code               4102153