Organocatalytic Asymmetric One-Pot Sequential Conjugate Addition/Dearomative Fluorination: Synthesis of Chiral Fluorinated Isoxazol-5(4H)-ones
Wen-Ting Meng; Yan Zheng; Jing Nie; Heng-Ying Xiong; Jun-An Ma; Journal of Organic Chemistry 78 (2013) 559–567; doi:10.1021/jo302419e

data_4027864
_publ_section_title
;
 Organocatalytic Asymmetric One-Pot Sequential Conjugate
 Addition/Dearomative Fluorination: Synthesis of Chiral Fluorinated
 Isoxazol-5(4H)-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              559
_journal_page_last               567
_journal_paper_doi               10.1021/jo302419e
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C17 H12 Br F N2 O4'
_chemical_formula_weight         407.20
_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                   7.5921(5)
_cell_length_b                   12.0779(9)
_cell_length_c                   18.0873(14)
_cell_measurement_reflns_used    4808
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1658.5(2)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_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      294(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'RIGAKU MERCURY375R'
_diffrn_measurement_method       'profile data from \w-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  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17320
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_T_max  0.6333
_exptl_absorpt_correction_T_min  0.2612
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.017(8)
_refine_ls_extinction_coef       0.0077(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   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0325P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                3002
_reflns_number_total             3782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302419e_si_002.cif
_cod_data_source_block           120421b
_cod_database_code               4027864