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_4026800
_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 rm
_chemical_formula_moiety         'C34 H32 F3 N O2'
_chemical_formula_sum            'C34 H32 F3 N O2'
_chemical_formula_weight         543.61
_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                 96.313(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.858(3)
_cell_length_b                   10.449(2)
_cell_length_c                   13.184(4)
_cell_measurement_reflns_used    1082
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      17.25
_cell_measurement_theta_min      2.45
_cell_volume                     1349.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.1120
_diffrn_reflns_av_sigmaI/netI    0.1316
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13246
_diffrn_reflns_theta_full        23.32
_diffrn_reflns_theta_max         23.32
_diffrn_reflns_theta_min         2.08
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         3704
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                2311
_reflns_number_total             3704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202009q_si_002.cif
_cod_data_source_block           1228GuillotICMMO
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026800