Tandem radical addition and cyclization of epsilon-substituted delta-yne ketimines.
Fernández, Marta; Alonso, Ricardo; Organic letters 7 (2005) 11–14; doi:10.1021/ol048104s

data_1506504
_publ_section_title
;
 Tandem radical addition and cyclization of epsilon-substituted delta-yne
 ketimines.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              11
_journal_page_last               14
_journal_paper_doi               10.1021/ol048104s
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration syn
_chemical_compound_source        'Synthetized from commercial glucuronolactone'
_chemical_formula_moiety         'C30 H31 N1 O5 S1'
_chemical_formula_sum            'C30 H31 N O5 S'
_chemical_formula_weight         517.62
_chemical_melting_point          441
_chemical_name_systematic
;
(3aR,4aS,5R,8aR,8bR)-2,2-dimethyl-8a(benzyloxyamino)-8-phenyl-7-
(phenylsulfanyl)-3a,4a,5,6,8a,8b-hexahydrobenzo[4,5]furo[2,3-d][1,3]dioxol-5-ol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.194(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9050(6)
_cell_length_b                   9.0569(7)
_cell_length_c                   13.2693(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.76
_cell_measurement_theta_min      18.95
_cell_volume                     1309.59(14)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1206
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3024
_diffrn_reflns_theta_full        74.91
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        -1
_diffrn_standards_interval_count 138
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.433
_exptl_absorpt_correction_T_max  0.9190
_exptl_absorpt_correction_T_min  0.5980
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method 'From dichloromethane-hexane'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0943P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                2387
_reflns_number_total             2872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048104ssi20041123_125614.cif
_cod_data_source_block           2000ra01
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1506504