Organocatalytic Oxyamination of Azlactones: Kinetic Resolution of Oxaziridines and Asymmetric Synthesis of Oxazolin-4-ones
Shunxi Dong; Xiaohua Liu; Yin Zhu; Peng He; Lili Lin; Xiaoming Feng; Journal of the American Chemical Society 135 (2013) 10026–10029; doi:10.1021/ja404379n

data_4120087
_publ_section_title
;
 Organocatalytic Oxyamination of Azlactones: Kinetic Resolution of
 Oxaziridines and Asymmetric Synthesis of Oxazolin-4-ones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10026
_journal_page_last               10029
_journal_paper_doi               10.1021/ja404379n
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C52 H80 N8 O2, 2(B F4)'
_chemical_formula_sum            'C52 H80 B2 F8 N8 O2'
_chemical_formula_weight         1022.86
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                   20.254(3)
_cell_length_b                   20.254(3)
_cell_length_c                   18.001(4)
_cell_measurement_reflns_used    20008
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      1.82
_cell_volume                     7384(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            54994
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.920
_exptl_crystal_description       plate
_exptl_crystal_F_000             2184
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_platon_squeeze_details
;
;
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.804
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6507
_refine_ls_number_restraints     444
_refine_ls_restrained_S_all      1.932
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.1263
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3066
_refine_ls_wR_factor_ref         0.3154
_reflns_number_gt                5212
_reflns_number_total             6507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja404379n_si_003.cif
_cod_data_source_block           a
_cod_database_code               4120087