Enantioselective Iridium-Catalyzed Imine Vinylation: Optically Enriched Allylic Amines via Alkyne-Imine Reductive Coupling Mediated by Hydrogen
Ming-Yu Ngai; Andriy Barchuk; Michael J. Krische; Journal of the American Chemical Society 129 (2007) 12644–12645; doi:10.1021/ja075438e

data_4110067
_publ_section_title
;
 Enantioselective Iridium-Catalyzed Imine Vinylation: Optically Enriched
 Allylic Amines via Alkyne-Imine Reductive Coupling Mediated by Hydrogen
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12644
_journal_page_last               12645
_journal_paper_doi               10.1021/ja075438e
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H18 Br N O2 S'
_chemical_formula_weight         380.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 96.030(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3477(4)
_cell_length_b                   9.7315(4)
_cell_length_c                   17.1742(9)
_cell_measurement_reflns_used    2946
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1719.85(13)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa 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  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9328
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    2.517
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'de Meulenaar, J., Tompa, H. (1965) Acta Cryst. A19, 1014-1018'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       needles
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6573
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.052
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0123P)^2^+2.9320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                4842
_reflns_number_total             6573
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja075438erom20070720_054334.cif
_cod_data_source_block           abiii82
_cod_database_code               4110067