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_4028109
_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         'C35 H33 N O4 S'
_chemical_formula_sum            'C35 H33 N O4 S'
_chemical_formula_weight         563.68
_space_group_IT_number           1
_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                94.1930(10)
_cell_angle_beta                 110.2980(10)
_cell_angle_gamma                113.9310(10)
_cell_formula_units_Z            1
_cell_length_a                   8.41850(10)
_cell_length_b                   10.16360(10)
_cell_length_c                   10.21290(10)
_cell_measurement_reflns_used    6368
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      31.02
_cell_measurement_theta_min      2.73
_cell_volume                     725.441(17)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12422
_diffrn_reflns_theta_full        31.02
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_correction_T_min  0.9416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             298
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         8187
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0631P)^2^+0.0074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                7697
_reflns_number_total             8187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400121j_si_004.cif
_cod_data_source_block           chan152s
_cod_original_cell_volume        725.441(13)
_cod_database_code               4028109