Enantioselective α-Arylation of N-Acyloxazolidinones with Copper(II)-bisoxazoline Catalysts and Diaryliodonium Salts
Aurélien Bigot; Alice E. Williamson; Matthew J. Gaunt; Journal of the American Chemical Society 133 (2011) 13778–13781; doi:10.1021/ja206047h

data_4106727
_publ_section_title
;
 Enantioselective \a-Arylation of N-Acyloxazolidinones with
 Copper(II)-bisoxazoline Catalysts and Diaryliodonium Salts
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13778
_journal_page_last               13781
_journal_paper_doi               10.1021/ja206047h
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration
;
 Flack parameter -0.011(6) 
;
_chemical_formula_moiety         'C17 H14 Br N O3'
_chemical_formula_sum            'C17 H14 Br N O3'
_chemical_formula_weight         360.20
_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                   5.8888(1)
_cell_length_b                   8.9545(1)
_cell_length_c                   28.5863(4)
_cell_measurement_reflns_used    15941
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      1.00
_cell_volume                     1507.39(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            13566
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    2.739
_exptl_absorpt_correction_T_max  0.540
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                4127
_reflns_number_total             4929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja206047h_si_002.cif
_cod_data_source_block           mg1107
_cod_database_code               4106727