Cyclization by Intramolecular Carbolithiation of Alkyl- and Vinyllithiums Prepared by the Action of Aromatic Radical Anions on Phenyl Thioethers. High Stereoselectivity in the Cyclization Accelerated by an Allylic Lithium Oxyanion
Kai Deng; Ahlem Bensari-Bouguerra; Joseph Whetstone; Theodore Cohen; Journal of Organic Chemistry 71 (2006) 2360–2372; doi:10.1021/jo052535m

data_4021569
_publ_section_title
;
 Cyclization by Intramolecular Carbolithiation of Alkyl- and Vinyllithiums
 Prepared by the Action of Aromatic Radical Anions on Phenyl
 Thioethers. High Stereoselectivity in the Cyclization Accelerated by
 an Allylic Lithium Oxyanion
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2360
_journal_page_last               2372
_journal_paper_doi               10.1021/jo052535m
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C20 H20 N2 O6 S'
_chemical_formula_weight         416.44
_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                 104.5240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6258(5)
_cell_length_b                   14.2621(7)
_cell_length_c                   13.7374(7)
_cell_measurement_temperature    200(2)
_cell_volume                     2015.32(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15858
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.476
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.476
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0780
_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^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1958
_refine_ls_wR_factor_ref         0.2067
_reflns_number_gt                2443
_reflns_number_total             3551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052535mrom20051209_102228.cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021569