Synthesis of Oxazoles by Tandem Cycloisomerization/Allylic Alkylation of Propargyl Amides with Allylic Alcohols: Zn(OTf)2 as π Acid and σ Acid Catalyst.
Wang, Bin; Chen, Ying; Zhou, Ling; Wang, Jianwu; Tung, Chen-Ho; Xu, Zhenghu; The Journal of organic chemistry 80 (2015) 12718–12724; doi:10.1021/acs.joc.5b02382

data_4036514
_publ_section_title
;
 Synthesis of Oxazoles by Tandem Cycloisomerization/Allylic Alkylation of
 Propargyl Amides with Allylic Alcohols: Zn(OTf)2 as \p Acid and \s Acid
 Catalyst.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12718
_journal_page_last               12724
_journal_paper_doi               10.1021/acs.joc.5b02382
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C26 H18 F3 N O'
_chemical_formula_weight         417.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.586(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.979(13)
_cell_length_b                   5.836(2)
_cell_length_c                   23.108(9)
_cell_measurement_temperature    298(2)
_cell_volume                     4284(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'bruker apex II'
_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  0.0698
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18201
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9904
_exptl_crystal_colour            PALE-YELLOW
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0636
_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^)+(0.0758P)^2^+4.9045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1560
_refine_ls_wR_factor_ref         0.1938
_reflns_number_gt                2125
_reflns_number_total             3757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02382_si_002.cif
_cod_data_source_block           p
_cod_database_code               4036514