Oxidant-Dependent Chemoselectivity in the Gold-Catalyzed Oxidative Cyclizations of 3,4,6,6-Tetrasubstituted 3,5-Dien-1-ynes
Hsiao-Hua Hung; Yi-Ching Liao; Rai-Shung Liu; Journal of Organic Chemistry 78 (2013) 7970–7976; doi:10.1021/jo401161h

data_4028500
_publ_section_title
;
 Oxidant-Dependent Chemoselectivity in the Gold-Catalyzed Oxidative
 Cyclizations of 3,4,6,6-Tetrasubstituted 3,5-Dien-1-ynes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7970
_journal_page_last               7976
_journal_paper_doi               10.1021/jo401161h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C19 H25 N O2 S'
_chemical_formula_weight         331.46
_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                61.9960(10)
_cell_angle_beta                 85.2350(10)
_cell_angle_gamma                68.6700(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3223(5)
_cell_length_b                   10.8288(5)
_cell_length_c                   11.3948(6)
_cell_measurement_reflns_used    2550
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.1257
_cell_measurement_theta_min      2.7534
_cell_volume                     940.65(8)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13766
_diffrn_reflns_theta_full        26.56
_diffrn_reflns_theta_max         26.56
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       Lump
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.1743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                2346
_reflns_number_total             3892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401161h_si_002.cif
_cod_data_source_block           mo_120557_0m
_cod_database_code               4028500