Synthesis of cis-3-Acyl-4-alkenylpyrrolidines via Gold(I)-Catalyzed Cycloisomerization Reaction of (Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols
Ming-Chang P. Yeh; Ming-Nan Lin; Wei-Jong Chang; Jia-Lun Liou; Ya-Fon Shih; Journal of Organic Chemistry 75 (2010) 6031–6034; doi:10.1021/jo101148e

data_4025643
_publ_section_title
;
 Synthesis of cis-3-Acyl-4-alkenylpyrrolidines via Gold(I)-Catalyzed
 Cycloisomerization Reaction of
 (Z)-8-Aryl-5-tosyl-5-azaoct-2-en-7-yn-1-ols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6031
_journal_page_last               6034
_journal_paper_doi               10.1021/jo101148e
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C21 H20 O1'
_chemical_formula_sum            'C21 H20 O'
_chemical_formula_weight         288.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5989(2)
_cell_length_b                   8.4736(3)
_cell_length_c                   34.6488(13)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1643.84(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0932
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            10789
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   7(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.1649
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1146P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.2008
_reflns_number_gt                1271
_reflns_number_total             2748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101148e_si_003_7.cif
_cod_data_source_block           a8860
_cod_database_code               4025643