Merging gold catalysis, organocatalytic oxidation, and lewis acid catalysis for chemodivergent synthesis of functionalized oxazoles from N-propargylamides
Mai, Shaoyu; Rao, Changqing; Chen, Ming; Su, Ji-Hu; Du, Jiangfeng; Song, Qiuling; Chem. Commun.  (2017) –; doi:10.1039/C7CC05746F

data_7120582
_publ_section_title
;
 Merging gold catalysis, organocatalytic oxidation, and lewis acid
 catalysis for chemodivergent synthesis of functionalized oxazoles from
 N-propargylamides
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC05746F
_journal_year                    2017
_chemical_formula_moiety         '0.22(C11 H8 N2 O)'
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2016-05-27 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.846(8)
_cell_angle_gamma                90
_cell_formula_units_Z            37
_cell_length_a                   7.8533(8)
_cell_length_b                   17.4662(14)
_cell_length_c                   13.5621(15)
_cell_measurement_temperature    293(2)
_cell_volume                     1842.9(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8281
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.866
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             814
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0673P)^2^+0.1308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2533
_reflns_number_total             3760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05746f2.cif
_cod_data_source_block           1
_cod_database_code               7120582
_shelxl_version_number           2014-1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C24(H24)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              58130
_olex2_submission_special_instructions 'No special instructions were received'