Enantioselective Cascade Reactions of Stable Sulfur Ylides and Nitroolefins through an Axial-to-Central Chirality Transfer Strategy
Liang-Qiu Lu; Zhi-Hui Ming; Jing An; Chao Li; Jia-Rong Chen; Wen-Jing Xiao; Journal of Organic Chemistry 77 (2012) 1072–1080; doi:10.1021/jo202324f

data_4026906
_publ_section_title
;
 Enantioselective Cascade Reactions of Stable Sulfur Ylides and
 Nitroolefins through an Axial-to-Central Chirality Transfer Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1072
_journal_page_last               1080
_journal_paper_doi               10.1021/jo202324f
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C16 H12 Br N O3'
_chemical_formula_weight         346.18
_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                 103.384(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9944(11)
_cell_length_b                   6.2207(9)
_cell_length_c                   14.801(2)
_cell_measurement_reflns_used    2843
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.68
_cell_measurement_theta_min      2.62
_cell_volume                     716.07(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7876
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    2.879
_exptl_absorpt_correction_T_max  0.9447
_exptl_absorpt_correction_T_min  0.3922
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      0
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0519P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2466
_reflns_number_total             3043
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202324f_si_001.cif
_cod_data_source_block           090104cm
_cod_original_cell_volume        716.05(18)
_cod_database_code               4026906