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_4028460
_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_sum            'C28 H38.5 Au F2 N2 O2.25 P'
_chemical_formula_weight         705.04
_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                 104.180(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.7732(6)
_cell_length_b                   15.9334(5)
_cell_length_c                   20.2459(7)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      31.01
_cell_measurement_theta_min      2.44
_cell_volume                     5871.5(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            67782
_diffrn_reflns_theta_full        31.06
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    5.106
_exptl_absorpt_correction_T_max  0.4283
_exptl_absorpt_correction_T_min  0.2346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       plate
_exptl_crystal_F_000             2804
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         4.488
_refine_diff_density_min         -3.890
_refine_diff_density_rms         0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     691
_refine_ls_number_reflns         18750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.8716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                12895
_reflns_number_total             18750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401083m_si_002.cif
_cod_data_source_block           chan166s
_cod_original_formula_sum        'C28 H38.50 Au F2 N2 O2.25 P'
_cod_database_code               4028460