Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines
Hu, Lin; Wu, Yongwei; Li, Zhe; Deng, Li; Journal of the American Chemical Society  (2016) –; doi:10.1021/jacs.6b09754

data_4125318
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Chiral \g-Amino Ketones via Umpolung
 Reactions of Imines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.6b09754
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H23 N1 O3'
_chemical_formula_sum            'C17 H23 N O3'
_chemical_formula_weight         289.37
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-28
_audit_creation_method           CRYSTALS_ver_14.61_build_00000
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2842(2)
_cell_length_b                   10.4412(3)
_cell_length_c                   28.9439(9)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100
_cell_measurement_theta_max      66
_cell_measurement_theta_min      5
_cell_volume                     1596.93(9)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            34041
_diffrn_reflns_theta_full        66.645
_diffrn_reflns_theta_max         66.646
_diffrn_reflns_theta_min         3.054
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details 'Flack (1983), 1118 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       33(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9795
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.0011928
_refine_ls_shift/su_mean         0.0001926
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 1.05P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0817
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0817
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                2381
_reflns_number_total             2777
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.68
_oxford_diffrn_Wilson_scale      22.54
_oxford_refine_ls_r_factor_ref   0.0471
_oxford_refine_ls_scale          0.22203(18)
_oxford_reflns_number_all        2777
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'zsl in P2(1)2(1)2(1)'
_cod_data_source_file            ja6b09754_si_004.cif
_cod_data_source_block           lhu_06_90_01
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C17 H23 N1 O3'
_cod_database_code               4125318