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_4120086
_publ_contact_author_name
;
;
_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 ad
_chemical_formula_moiety         'C30 H25 Cl N2 O5 S, C H2 Cl2'
_chemical_formula_sum            'C31 H27 Cl3 N2 O5 S'
_chemical_formula_weight         645.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
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  Olex2 1.1
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_cell_measurement_temperature    293(2)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
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_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
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SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
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SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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_diffrn_measured_fraction_theta_full 0.998
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  1 omega   -9.00   19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8924  -99.0000   90.0000 28

  2 omega   -2.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   38.0000 -180.0000 88

  3 omega  -19.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   20.0000  120.0000 93

  4 omega  -47.00  -22.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8924   77.0000   60.0000 25
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_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_13      0.0426624000
_diffrn_orient_matrix_UB_21      -0.0324664000
_diffrn_orient_matrix_UB_22      -0.0116386000
_diffrn_orient_matrix_UB_23      0.0353565000
_diffrn_orient_matrix_UB_31      -0.0051269000
_diffrn_orient_matrix_UB_32      -0.0712650000
_diffrn_orient_matrix_UB_33      -0.0151127000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0502
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_diffrn_reflns_limit_l_min       -16
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_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'Enhance (Mo) x-ray Source'
_diffrn_source_current           n/a
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_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  1.00000
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
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empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     380
_refine_ls_number_reflns         4903
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.1573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                3774
_reflns_number_total             4903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja404379n_si_002.cif
_cod_data_source_block           120214_s1_dsx
_cod_original_cell_volume        1515.19(11)
_cod_database_code               4120086
_chemical_oxdiff_formula         C20H22O5N1S2Cl1
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32