Base-Catalyzed Cyclization of N-Sulfonyl Propargylamides to Sulfonylmethyl-Substituted Oxazoles via Sulfonyl Migration
Xinzhang Yu; Xiaoyi Xin; Boshun Wan; Xingwei Li; Journal of Organic Chemistry 78 (2013) 4895–4904; doi:10.1021/jo4004635

data_4028232
_publ_section_title
;
 Base-Catalyzed Cyclization of N-Sulfonyl Propargylamides to
 Sulfonylmethyl-Substituted Oxazoles via Sulfonyl Migration
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4895
_journal_page_last               4904
_journal_paper_doi               10.1021/jo4004635
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C29 H23 N O3 S'
_chemical_formula_weight         465.54
_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                90.00
_cell_angle_beta                 103.932(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3447(15)
_cell_length_b                   8.4511(11)
_cell_length_c                   23.555(3)
_cell_measurement_temperature    296(2)
_cell_volume                     2385.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13178
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0564P)^2^+0.5155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                3580
_reflns_number_total             4186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4004635_si_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4028232