Diastereoselective and Enantioselective Desymmetrization of α-Substituted Cyclohexadienones via Intramolecular Stetter Reaction
Min-Qiang Jia; Chuan Liu; Shu-Li You; Journal of Organic Chemistry 77 (2012) 10996–11001; doi:10.1021/jo3022555

data_4027776
_publ_section_title
;
 Diastereoselective and Enantioselective Desymmetrization of
 \a-Substituted Cyclohexadienones via Intramolecular Stetter Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10996
_journal_page_last               11001
_journal_paper_doi               10.1021/jo3022555
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H16 I N O3'
_chemical_formula_weight         433.23
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 105.319(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2395(6)
_cell_length_b                   11.7179(10)
_cell_length_c                   10.5844(9)
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.510
_cell_measurement_theta_min      5.292
_cell_volume                     865.99(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5236
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    1.865
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66029
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0144P)^2^+0.4808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0577
_reflns_number_gt                2772
_reflns_number_total             2826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3022555_si_002.cif
_cod_data_source_block           cd212133
_cod_database_code               4027776