Gold-Catalyzed Domino Aminocyclization/1,3-Sulfonyl Migration of N-Substituted N-Sulfonyl-aminobut-3-yn-2-ols to 1-Substituted 3-Sulfonyl-1H-pyrroles
Wan Teng Teo; Weidong Rao; Ming Joo Koh; Philip Wai Hong Chan; Journal of Organic Chemistry 78 (2013) 7508–7517; doi:10.1021/jo401083m

data_4028462
_publ_section_title
;
 Gold-Catalyzed Domino Aminocyclization/1,3-Sulfonyl Migration of
 N-Substituted N-Sulfonyl-aminobut-3-yn-2-ols to 1-Substituted
 3-Sulfonyl-1H-pyrroles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7508
_journal_page_last               7517
_journal_paper_doi               10.1021/jo401083m
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C33 H29 N O2 S, 0.25(C H2 Cl2)'
_chemical_formula_sum            'C33.25 H29.5 Cl0.5 N O2 S'
_chemical_formula_weight         524.86
_chemical_name_systematic
; 
 ? 
;
_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                102.154(3)
_cell_angle_beta                 90.787(4)
_cell_angle_gamma                103.190(4)
_cell_formula_units_Z            4
_cell_length_a                   9.8047(11)
_cell_length_b                   15.1178(19)
_cell_length_c                   19.350(3)
_cell_measurement_reflns_used    2154
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      2.59
_cell_volume                     2724.1(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0927
_diffrn_reflns_av_sigmaI/netI    0.1190
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35445
_diffrn_reflns_theta_full        26.24
_diffrn_reflns_theta_max         26.24
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             1106
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     718
_refine_ls_number_reflns         10715
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1164P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.2165
_reflns_number_gt                6371
_reflns_number_total             10715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401083m_si_004.cif
_cod_data_source_block           chan205
_cod_original_cell_volume        2724.2(6)
_cod_original_formula_sum        'C33.25 H29.50 Cl0.50 N O2 S'
_cod_database_code               4028462