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_4125319
_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         'C16 H23 N1 O3'
_chemical_formula_sum            'C16 H23 N O3'
_chemical_formula_weight         277.36
_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                   5.34400(10)
_cell_length_b                   10.8072(3)
_cell_length_c                   26.8774(7)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    100
_cell_measurement_theta_max      67
_cell_measurement_theta_min      3
_cell_volume                     1552.27(7)
_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 0.976
_diffrn_measured_fraction_theta_max 0.976
_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     1.54178
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            29134
_diffrn_reflns_theta_full        66.858
_diffrn_reflns_theta_max         66.858
_diffrn_reflns_theta_min         3.288
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.11
_refine_ls_abs_structure_details 'Flack (1983), 1050 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.06(14)
_refine_ls_extinction_coef       34(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.0004485
_refine_ls_shift/su_mean         0.0000773
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.24P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0613
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0613
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                2607
_reflns_number_total             2709
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0265
_oxford_refine_ls_scale          0.7358(17)
_oxford_reflns_number_all        2709
_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_003.cif
_cod_data_source_block           lhu_06_95_02
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C16 H23 N1 O3'
_cod_database_code               4125319