Catalytic, Enantioselective Intramolecular Hydroamination of Primary Amines Tethered to Di- and Trisubstituted Alkenes
Yulia Chapurina; Houssein Ibrahim; Régis Guillot; Emilie Kolodziej; Jacqueline Collin; Alexander Trifonov; Emmanuelle Schulz; Jérôme Hannedouche; Journal of Organic Chemistry 76 (2011) 10163–10172; doi:10.1021/jo202009q

data_4026801
_publ_contact_author_address
;Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay,
CNRS
UMR 8182,
B\^at.420,
Universit\'e Paris-Sud
91405 Orsay cedex,
France. 
;
_publ_contact_author_email       jerome.hannedouche@u-psud.fr
_publ_contact_author_fax         '+33 (0)1 6915 4680 '
_publ_contact_author_name        'J\'er\^ome Hannedouche'
_publ_contact_author_phone       '+33 (0)1 6915 4740'
_publ_section_title
;
 Catalytic, Enantioselective Intramolecular Hydroamination of Primary
 Amines Tethered to Di- and Trisubstituted Alkenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10163
_journal_page_last               10172
_journal_paper_doi               10.1021/jo202009q
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C68 H52 N4 Y, C16 H31 Li O4'
_chemical_formula_sum            'C84 H83 Li N4 O4 Y'
_chemical_formula_weight         1308.39
_chemical_properties_physical    'air-sensitive, oxygen-sensitive'
_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                 90.890(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3717(8)
_cell_length_b                   26.868(3)
_cell_length_c                   12.3492(12)
_cell_measurement_reflns_used    7265
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.24
_cell_volume                     3440.9(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_sigmaI/netI    0.1551
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41959
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.65
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.903
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       plate
_exptl_crystal_F_000             1378
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     847
_refine_ls_number_reflns         14643
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                9341
_reflns_number_total             14643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202009q_si_003.cif
_cod_data_source_block           937GuillotICMMO
_cod_original_cell_volume        3440.8(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C84 H83 Li1 N4 O4 Y1'
_cod_database_code               4026801