Highly Enantioselective Hydrogenation of α-Arylmethylene Cycloalkanones Catalyzed by Iridium Complexes of Chiral Spiro Aminophosphine Ligands
Jian-Bo Xie; Jian-Hua Xie; Xiao-Yan Liu; Wei-Ling Kong; Shen Li; Qi-Lin Zhou; Journal of the American Chemical Society 132 (2010) 4538–4539; doi:10.1021/ja100652f

data_4102216
_publ_section_title
;
 Highly Enantioselective Hydrogenation of \a-Arylmethylene Cycloalkanones
 Catalyzed by Iridium Complexes of Chiral Spiro Aminophosphine Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4538
_journal_page_last               4539
_journal_paper_doi               10.1021/ja100652f
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C12 H15 Br O'
_chemical_formula_weight         255.15
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2487(10)
_cell_length_b                   9.0689(18)
_cell_length_c                   23.581(5)
_cell_measurement_temperature    113(2)
_cell_volume                     1122.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9353
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    3.628
_exptl_absorpt_correction_T_max  0.6306
_exptl_absorpt_correction_T_min  0.5307
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(10)
_refine_ls_extinction_coef       0.0262(15)
_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   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0254P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0644
_reflns_number_gt                2203
_reflns_number_total             2656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja100652f_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1122.4(4)
_cod_database_code               4102216