Asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides through dynamic kinetic resolution
Echeverria, Pierre-Georges; Cornil, Johan; Ferard, Charlene; Guérinot, Amandine; Cossy, Janine; Phansavath, Phannarath; Vidal, Virginie; RSC Adv.  (2015) –; doi:10.1039/C5RA10385A

data_7220846
_publ_section_title
;
 Asymmetric transfer hydrogenation of \a-amino \b-keto ester
 hydrochlorides through dynamic kinetic resolution
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA10385A
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 N1 O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.33
_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   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2015-05-29 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.783(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6565(9)
_cell_length_b                   5.2736(4)
_cell_length_c                   13.0287(10)
_cell_measurement_reflns_used    985
_cell_measurement_temperature    200
_cell_measurement_theta_max      59
_cell_measurement_theta_min      3
_cell_volume                     777.83(11)
_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      200
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.039
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3892
_diffrn_reflns_theta_full        59.092
_diffrn_reflns_theta_max         59.092
_diffrn_reflns_theta_min         3.493
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.30
_refine_ls_abs_structure_details 'Flack (1983), 867 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9841
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2103
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.0021021
_refine_ls_shift/su_mean         0.0001733
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 3.65 4.53 1.26 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1231
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1231
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              5
_reflns_limit_k_min              -5
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1691
_reflns_number_total             2106
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.76
_oxford_diffrn_Wilson_scale      9.24
_oxford_refine_ls_r_factor_ref   0.0652
_oxford_refine_ls_scale          0.3715(7)
_oxford_reflns_number_all        2103
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c5ra10385a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21 '
_cod_original_formula_sum        'C17 H17 N1 O4'
_cod_database_code               7220846