Highly Enantioselective and Diastereoselective Synthesis of Chiral Amino Alcohols by Ruthenium-Catalyzed Asymmetric Hydrogenation of α-Amino Aliphatic Ketones
Jian-Hua Xie; Sheng Liu; Wei-Ling Kong; Wen-Ju Bai; Xiao-Chen Wang; Li-Xin Wang; Qi-Lin Zhou; Journal of the American Chemical Society 131 (2009) 4222–4223; doi:10.1021/ja901058u

data_4104110
_publ_section_title
;
 Highly Enantioselective and Diastereoselective Synthesis of Chiral Amino
 Alcohols by Ruthenium-Catalyzed Asymmetric Hydrogenation of \a-Amino
 Aliphatic Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4222
_journal_page_last               4223
_journal_paper_doi               10.1021/ja901058u
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H18 Br N O'
_chemical_formula_sum            'C13 H18 Br N O'
_chemical_formula_weight         284.19
_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                 99.744(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1637(12)
_cell_length_b                   7.3171(8)
_cell_length_c                   10.0120(14)
_cell_measurement_reflns_used    1753
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.1
_cell_volume                     661.64(15)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6777
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    3.087
_exptl_absorpt_correction_T_max  0.7903
_exptl_absorpt_correction_T_min  0.5772
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
    ENTER TEXT OF LETTER 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
'Flack H D (1983), 1063 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(9)
_refine_ls_extinction_coef       0.0137(17)
_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   0.861
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.861
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0273
_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^)+(0.0203P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0594
_reflns_number_gt                1183
_reflns_number_total             2323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja901058u_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4104110