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_4117866
_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_formula_sum            'C25 H Cl4 N O3 Zr'
_chemical_formula_weight         596.29
_chemical_name_systematic
;
 ?
;
_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                   8.0419(15)
_cell_length_b                   13.342(2)
_cell_length_c                   18.841(4)
_cell_measurement_temperature    100(2)
_cell_volume                     2021.5(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8246
_diffrn_reflns_theta_full        30.48
_diffrn_reflns_theta_max         30.48
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    1.106
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_F_000             1160
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0301P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                4605
_reflns_number_total             5691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja302552e_si_004.cif
_cod_data_source_block           th_5_15_0m
_cod_database_code               4117866