Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters
Kunru Yu; Xiaohua Liu; Xiaobin Lin; Lili Lin; Xiaoming Feng; Chem.Commun. 51 (2015) 14897–; doi:10.1039/C5cc05534B

data_7117855
_publ_section_title
;
 Organocatalytic dynamic kinetic resolution of azlactones to construct
 chiral N-acyl amino acid oxime esters
;
_journal_name_full               Chem.Commun.
_journal_page_first              14897
_journal_paper_doi               10.1039/C5cc05534B
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '2(C20 H22 N2 O3), 0.5(C4 H8 O2)'
_chemical_formula_sum            'C42 H48 N4 O7'
_chemical_formula_weight         720.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
_audit_creation_date             2015-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_audit_update_record
;
2015-03-31 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.696(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8877(3)
_cell_length_b                   21.2513(5)
_cell_length_c                   11.0106(4)
_cell_measurement_reflns_used    8089
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.0560
_cell_measurement_theta_min      4.6450
_cell_volume                     2204.14(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega  -52.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000 -180.0000 87

  2 omega   -2.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486   19.0000   90.0000 110

  3 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -99.0000  -90.0000 75

  4 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486 -125.0000 -150.0000 67

  5 omega  -34.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -77.0000  -60.0000 98

  6 omega    7.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486   77.0000  -90.0000 98

  7 omega   15.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486 -115.0000  102.0000 70

  8 omega  -36.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486    0.0000 -180.0000 143

  9 omega   13.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486   38.0000  120.0000 93

 10 omega   17.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486   57.0000   30.0000 87

 11 omega  -35.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -38.0000   90.0000 93

 12 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -99.0000  -30.0000 75

 13 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -99.0000  -60.0000 75

 14 omega  -33.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -57.0000  150.0000 87

 15 omega   38.00   98.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 60

 16 omega   37.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 54

 17 omega   38.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 71

 18 omega   37.00  115.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 19 omega   38.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 71

 20 omega   57.00  150.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 93

 21 omega   37.00  115.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 22 omega   79.00  177.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 98

 23 omega   38.00   98.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 60

 24 omega   37.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 54

 25 omega   37.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 54

 26 omega   37.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 54

 27 omega   53.00   78.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 25

 28 omega   42.00   86.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 44

 29 omega   37.00   76.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 39

 30 omega   77.00  177.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 100

 31 omega   59.00  107.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 48

 32 omega   39.00   90.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 51

 33 omega   41.00  125.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 84

 34 omega   94.00  144.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0721532000
_diffrn_orient_matrix_UB_12      -0.0595126000
_diffrn_orient_matrix_UB_13      -0.0702992000
_diffrn_orient_matrix_UB_21      -0.0720441000
_diffrn_orient_matrix_UB_22      0.0398238000
_diffrn_orient_matrix_UB_23      -0.1190290000
_diffrn_orient_matrix_UB_31      0.1278661000
_diffrn_orient_matrix_UB_32      -0.0111363000
_diffrn_orient_matrix_UB_33      -0.0496878000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24270
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.346
_diffrn_reflns_theta_min         4.161
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 2793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8517
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1370P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1955
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                6820
_reflns_number_total             8517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05534b2.cif
_cod_data_source_block           fxm-ykr-24-3-2
_cod_original_cell_volume        2204.15(12)
_cod_database_code               7117855
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O01F(0.5) O01G(0.5) C01H(0.5) H01O(0.5) H01P(0.5) C1(0.5) C2(0.5)
 H2A(0.5) H2B(0.5) H2C(0.5) C3(0.5) H3A(0.5) H3B(0.5) H3C(0.5)
3.a Ternary CH refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00T(H00T), C00Y(H00Y)
3.b Secondary CH2 refined with riding coordinates:
 C00M(H00C,H00D), C00Q(H00A,H00B), C01H(H01O,H01P)
3.c Aromatic/amide H refined with riding coordinates:
 N003(H003), N006(H006), C00J(H00J), C00L(H00L), C00N(H00N), C00P(H00P),
 C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015), C017(H017), C018(H018), C019(H019), C01D(H01M), C01E(H01N)
3.d Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C), C01A(H01G,H01H,H01I), C01B(H01D,H01E,H01F), C01C(H01J,
 H01K,H01L), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              14100
_shelx_hkl_checksum              79845
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'