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_4028233
_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            'C25 H23 N O4 S'
_chemical_formula_weight         433.50
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.059(3)
_cell_angle_beta                 90.014(4)
_cell_angle_gamma                98.644(3)
_cell_formula_units_Z            4
_cell_length_a                   11.3247(7)
_cell_length_b                   12.8430(7)
_cell_length_c                   15.8094(9)
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.03
_cell_measurement_theta_min      2.58
_cell_volume                     2273.2(2)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Smart Apex II CCD'
_diffrn_measurement_method       '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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13128
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9938
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         7591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0645
_refine_ls_shift/su_max          0.088
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1236P)^2^+0.1064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.2144
_reflns_number_gt                4853
_reflns_number_total             7591
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4004635_si_003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4028233