Gold-Catalyzed Stereoselective Synthesis of Bicyclic Lactams and Ketones from N-Tosylynamidomethyl-Tethered Cyclohexenes.
Zhong, Chang-Zhi; Tung, Po-Ting; Chao, Tsung-Han; Yeh, Ming-Chang P; The Journal of organic chemistry 82 (2017) 481–501; doi:10.1021/acs.joc.6b02479

data_4032231
_publ_section_title
;
 Gold-Catalyzed Stereoselective Synthesis of Bicyclic Lactams and Ketones
 from N-Tosylynamidomethyl-Tethered Cyclohexenes.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              481
_journal_page_last               501
_journal_paper_doi               10.1021/acs.joc.6b02479
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C23 H25 N O5 S'
_chemical_formula_sum            'C23 H25 N O5 S'
_chemical_formula_weight         427.50
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.588(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0902(6)
_cell_length_b                   14.6898(15)
_cell_length_c                   23.027(3)
_cell_measurement_reflns_used    1075
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      19.82
_cell_measurement_theta_min      2.91
_cell_volume                     2059.3(4)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.1178
_diffrn_reflns_av_sigmaI/netI    0.1292
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14544
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.8880
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                1788
_reflns_number_total             3642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02479_si_004.cif
_cod_data_source_block           a16616
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4032231