Asymmetric Synthesis of 8-Aminoindolizidine from Chiral 2-Pyrroleimines
Vincenzo Giulio Albano; Andrea Gualandi; Magda Monari; Diego Savoia; Journal of Organic Chemistry 73 (2008) 8376–8381; doi:10.1021/jo8014598

data_4023807
_publ_section_title
;
 Asymmetric Synthesis of 8-Aminoindolizidine
 from Chiral 2-Pyrroleimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8376
_journal_page_last               8381
_journal_paper_doi               10.1021/jo8014598
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H24 N2 O2'
_chemical_formula_weight         252.35
_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                 97.2260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1635(7)
_cell_length_b                   10.3337(11)
_cell_length_c                   23.006(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1453.7(3)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    'ORTEP-3 (Farrugia 2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Giacovazzo, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART Apex II CCD'
_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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9055
_diffrn_reflns_theta_full        24.12
_diffrn_reflns_theta_max         24.12
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         2455
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0481P)^2^+0.5097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1183
_reflns_number_gt                1878
_reflns_number_total             2455
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8014598_si_001.cif
_cod_data_source_block           (S,R)14a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023807