A Simple Method for Asymmetric Trifluoromethylation of N-Acyl Oxazolidinones via Ru-Catalyzed Radical Addition to Zirconium Enolates
Aaron T. Herrmann; Lindsay L. Smith; Armen Zakarian; Journal of the American Chemical Society 134 (2012) 6976–6979; doi:10.1021/ja302552e

data_4117865
_publ_section_title
;
 A Simple Method for Asymmetric Trifluoromethylation of N-Acyl
 Oxazolidinones via Ru-Catalyzed Radical Addition to Zirconium Enolates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6976
_journal_page_last               6979
_journal_paper_doi               10.1021/ja302552e
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H18 F7 N O3'
_chemical_formula_weight         429.33
_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                 112.269(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8702(10)
_cell_length_b                   10.2362(9)
_cell_length_c                   15.4223(14)
_cell_measurement_temperature    100(2)
_cell_volume                     1880.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX'
_diffrn_measurement_method       'Omega scan'
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22610
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.589
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         11098
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.589
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0592
_reflns_number_gt                10213
_reflns_number_total             11098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja302552e_si_003.cif
_cod_data_source_block           l11012011_0m
_cod_database_code               4117865