Tandem Nucleophilic Addition/Oxy-2-azonia-Cope Rearrangement for the Formation of Homoallylic Amides and Lactams: Total Synthesis and Structural Verification of Motuporamine G
Lijun Zhou; Zhiming Li; Yue Zou; Quanrui Wang; Italo A. Sanhueza; Franziska Schoenebeck; Andreas Goeke; Journal of the American Chemical Society 134 (2012) 20009–20012; doi:10.1021/ja310002m

data_4119006
_publ_section_title
;
 Tandem Nucleophilic Addition/Oxy-2-azonia-Cope Rearrangement for the
 Formation of Homoallylic Amides and Lactams: Total Synthesis and
 Structural Verification of Motuporamine G
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20009
_journal_page_last               20012
_journal_paper_doi               10.1021/ja310002m
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C19 H26 N2 O5 S'
_chemical_formula_weight         394.48
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 101.543(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.751(2)
_cell_length_b                   10.752(3)
_cell_length_c                   14.225(5)
_cell_measurement_reflns_used    920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.215
_cell_measurement_theta_min      2.392
_cell_volume                     1011.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4935
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0605P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                2899
_reflns_number_total             3888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310002m_si_005.cif
_cod_data_source_block           a20717a
_cod_original_cell_volume        1011.6(6)
_cod_database_code               4119006