Intermolecular, Catalytic Asymmetric Hydroamination of Bicyclic Alkenes and Dienes in High Yield and Enantioselectivity
Jianrong (Steve) Zhou; John F. Hartwig; Journal of the American Chemical Society 130 (2008) 12220–12221; doi:10.1021/ja803523z

data_4108339
_publ_contact_author             'John F. Hartwig'
_publ_contact_author_email       jhartwig@uiuc.edu
_publ_section_title
;
 Intermolecular, Catalytic Asymmetric Hydroamination of Bicyclic Alkenes
 and Dienes in High Yield and Enantioselectivity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12220
_journal_page_last               12221
_journal_paper_doi               10.1021/ja803523z
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H16 Br N'
_chemical_formula_sum            'C13 H16 Br N'
_chemical_formula_weight         266.18
_chemical_name_common            N-(2-exo-norbornyl)-p-bromoaniline
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2007-09-21   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8653(5)
_cell_length_b                   7.5844(7)
_cell_length_c                   26.955(2)
_cell_measurement_reflns_used    1446
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      2.69
_cell_volume                     1199.09(17)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2005)'
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \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_radiation_wavelength_id  ga74vas
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6168
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    3.396
_exptl_absorpt_correction_T_max  0.9271
_exptl_absorpt_correction_T_min  0.1848
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       platy
_exptl_crystal_F_000             544
_exptl_crystal_id                ga74vas
_exptl_crystal_preparation
; 
The data crystal was mounted using epoxy to a 0.3 mm cryo-loop 
(Hampton Research) with the (0 4 3) scattering planes roughly normal 
to the spindle axis. 
;
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack (1983),  867 Friedels'
_refine_ls_abs_structure_Flack   0.009(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.860
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0256P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0515
_refine_ls_wR_factor_ref         0.0580
_reflns_number_gt                1295
_reflns_number_total             2164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja803523z_si_001.cif
_cod_data_source_block           bromoanilineadduct
_cod_original_cell_volume        1199.11(18)
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4108339