A Stereoselective Hydroamination Transform To Access Polysubstituted Indolizidines
Sergey V. Pronin; M. Greg Tabor; Daniel J. Jansen; Ryan A. Shenvi; Journal of the American Chemical Society 134 (2012) 2012–2015; doi:10.1021/ja211090n

data_4117410
_publ_section_title
;
 A Stereoselective Hydroamination Transform To Access Polysubstituted
 Indolizidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2012
_journal_page_last               2015
_journal_paper_doi               10.1021/ja211090n
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C15 H30 N, C6 H2 N3 O7'
_chemical_formula_sum            'C21 H32 N4 O7'
_chemical_formula_weight         452.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.740(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9857(8)
_cell_length_b                   18.1370(19)
_cell_length_c                   15.7831(15)
_cell_measurement_reflns_used    4037
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.59
_cell_volume                     2285.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11838
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       Block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0819P)^2^+0.8936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1597
_reflns_number_gt                3284
_reflns_number_total             4647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211090n_si_003.cif
_cod_data_source_block           shenvi04
_cod_database_code               4117410