Gold-Catalyzed Cycloisomerization of 1,7-Enyne Esters to Structurally Diverse cis-1,2,3,6-Tetrahydropyridin-4-yl Ketones
Weidong Rao; Sally; Ming Joo Koh; Philip Wai Hong Chan; Journal of Organic Chemistry 78 (2013) 3183–3195; doi:10.1021/jo400121j

data_4028107
_publ_section_title
;
 Gold-Catalyzed Cycloisomerization of 1,7-Enyne Esters to Structurally
 Diverse cis-1,2,3,6-Tetrahydropyridin-4-yl Ketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3183
_journal_page_last               3195
_journal_paper_doi               10.1021/jo400121j
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H31 N O3 S'
_chemical_formula_sum            'C33 H31 N O3 S'
_chemical_formula_weight         521.65
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.663(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0919(3)
_cell_length_b                   12.6482(4)
_cell_length_c                   11.9258(4)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.95
_cell_measurement_theta_min      2.71
_cell_volume                     1366.88(8)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32648
_diffrn_reflns_theta_full        31.28
_diffrn_reflns_theta_max         31.28
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.9440
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         7962
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0757P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                7271
_reflns_number_total             7962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400121j_si_002.cif
_cod_data_source_block           chan137
_cod_database_code               4028107