Tantalum Catalyzed Hydroaminoalkylation for the Synthesis of α- and β-SubstitutedN-Heterocycles
Payne, Philippa R.; Garcia, Pierre; Eisenberger, Patrick; Yim, Jacky C.-H.; Schafer, Laurel L.; Organic Letters 15 (2013) 2182–; doi:10.1021/ol400729v

data_1511953
_publ_section_title
;
 Tantalum Catalyzed Hydroaminoalkylation for the Synthesis of \a- and
 \b-SubstitutedN-Heterocycles
;
_journal_issue                   9
_journal_name_full               'Organic Letters'
_journal_page_first              2182
_journal_paper_doi               10.1021/ol400729v
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C30 H37 N O3 S'
_chemical_formula_sum            'C30 H37 N O3 S'
_chemical_formula_weight         491.67
_chemical_name_systematic
2-(5-(benzhydryloxy)pentan-2-yl)-1-tosylpiperidine
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 102.122(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3640(2)
_cell_length_b                   37.836(1)
_cell_length_c                   11.2212(5)
_cell_measurement_reflns_used    6565
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.960
_cell_measurement_theta_min      2.461
_cell_volume                     2641.69(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18782
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.93
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             1056
_exptl_crystal_recrystallization_method 'Ethyl Acetate'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0454P)^2^+0.9163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                4656
_reflns_number_total             6014
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol400729v_si_002.cif
_cod_data_source_block           ls260_0m
_cod_original_cell_volume        2641.7(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1511953