Facile synthesis of polysubstituted oxazoles via a copper-catalyzed tandem oxidative cyclization.
Wan, Changfeng; Zhang, Jintang; Wang, Sujing; Fan, Jinmin; Wang, Zhiyong; Organic letters 12 (2010) 2338–2341; doi:10.1021/ol100688c

data_1502974
_publ_section_title
;
 Facile synthesis of polysubstituted oxazoles via a copper-catalyzed
 tandem oxidative cyclization.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2338
_journal_page_last               2341
_journal_paper_doi               10.1021/ol100688c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.450(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   6.715(5)
_cell_length_b                   17.086(5)
_cell_length_c                   16.786(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1917.2(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0763
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10174
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3916
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0123P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0595
_reflns_number_gt                1773
_reflns_number_total             3916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100688c_si_002.cif
_cod_data_source_block           wan090912
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1502974