Catalytic hetero-ene reactions of 5-methyleneoxazolines: highly enantioselective synthesis of 2,5-disubstituted oxazole derivatives
Weiwei Luo; Jiannan Zhao; Chengkai Yin; Xiaohua Liu; Lili Lin; Xiaoming Feng; Chem.Commun. 50 (2014) 7524–; doi:10.1039/C4CC02809K

data_7114640
_publ_section_title
;
 Catalytic hetero-ene reactions of 5-methyleneoxazolines: highly
 enantioselective synthesis of 2,5-disubstituted oxazole derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              7524
_journal_paper_doi               10.1039/C4CC02809K
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.997(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4062(14)
_cell_length_b                   7.4146(14)
_cell_length_c                   16.172(3)
_cell_measurement_reflns_used    1761
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.709
_cell_measurement_theta_min      5.955
_cell_volume                     887.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5278
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.986
_diffrn_reflns_theta_min         2.520
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
; 
 Flack x determined using 853 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   2.4(10)
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0451P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                2453
_reflns_number_total             3329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc02809k2.cif
_cod_data_source_block           cd214140
_cod_database_code               7114640
_shelxl_version_number           2013-4
_shelx_res_checksum              23156
_shelx_hkl_checksum              13025