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_4028110
_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         'C38 H39 N O4 S'
_chemical_formula_sum            'C38 H39 N O4 S'
_chemical_formula_weight         605.76
_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                107.990(6)
_cell_angle_beta                 92.021(6)
_cell_angle_gamma                92.084(6)
_cell_formula_units_Z            2
_cell_length_a                   10.8387(10)
_cell_length_b                   12.1976(10)
_cell_length_c                   13.2644(11)
_cell_measurement_reflns_used    3341
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      20.03
_cell_measurement_theta_min      2.54
_cell_volume                     1664.8(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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0644
_diffrn_reflns_av_sigmaI/netI    0.1245
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22048
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     801
_refine_ls_number_reflns         13007
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0897
_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^)+(0.1363P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2183
_refine_ls_wR_factor_ref         0.2476
_reflns_number_gt                8943
_reflns_number_total             13007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400121j_si_005.cif
_cod_data_source_block           chan162r
_cod_original_cell_volume        1664.8(2)
_cod_database_code               4028110