Organocatalytic enantio- and diastereoselective synthesis of 3,5-disubstituted prolines.
Riaño, Iker; Díaz, Estibaliz; Uria, Uxue; Reyes, Efraím; Carrillo, Luisa; Vicario, Jose L.; Chemical communications (Cambridge, England) 52 (2016) 2330–2333; doi:10.1039/c5cc09329e

data_7118347
_publ_section_title
;
 Organocatalytic enantio- and diastereoselective synthesis of
 3,5-disubstituted prolines.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2330
_journal_page_last               2333
_journal_paper_doi               10.1039/c5cc09329e
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H23 N1 O6'
_chemical_formula_sum            'C17 H23 N O6'
_chemical_formula_weight         337.36
_chemical_name_systematic
;
 dimethyl (3S,5S)-3-(2,6-dimethoxyphenyl)-5-methylpyrrolidine-
2,2-dicarboxylate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_date             2013-08-10T08:03:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2013-08-27 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.22300(10)
_cell_length_b                   7.16940(10)
_cell_length_c                   13.32590(10)
_cell_measurement_reflns_used    13321
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9279
_cell_measurement_theta_min      3.3175
_cell_measurement_wavelength     1.54184
_cell_volume                     880.153(17)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2010)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4023
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -91.00  -65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  125.0000   90.0000 26

  2 omega  -60.00  -20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -38.0000  -60.0000 40

  3 omega  -26.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631  -38.0000   90.0000 93

  4 omega   12.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   57.0000   30.0000 96

  5 omega  -33.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631  -57.0000 -120.0000 99

  6 omega  -40.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000 -120.0000 25

  7 omega  -86.00  -60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -45.0000  -90.0000 26

  8 omega  -80.00  -50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 30

  9 omega   39.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -49.0000  -44.0000 40

 10 omega   80.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000    0.0000 33

 11 omega   36.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000   90.0000 34

 12 omega  122.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000    0.0000 34

 13 omega   79.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   30.0000   60.0000 57

 14 omega   33.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  120.0000 35

 15 omega   30.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -150.0000 35

 16 omega   81.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000    0.0000 44

 17 omega   31.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000 -180.0000 32

 18 omega  114.00  147.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -60.0000 33

 19 omega   75.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -60.0000 32

 20 omega   30.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 25

 21 omega   76.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  -90.0000 60

 22 omega   35.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000  150.0000 86

 23 omega   88.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   90.0000 40

 24 omega  131.00  157.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   90.0000 26

 25 omega   35.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -49.0000 -103.0000 47

 26 omega   84.00  151.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -180.0000 67

 27 omega   36.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631 -125.0000   60.0000 26

 28 omega   41.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000    0.0000 30

 29 omega   64.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000    0.0000 38

 30 omega   64.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000 -150.0000 57

 31 omega   59.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   60.0000 26

 32 omega   68.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -90.0000 34

 33 omega   55.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -120.0000 29

 34 omega  124.00  156.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  125.0000  -30.0000 32

 35 omega  -74.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631   77.0000   60.0000 112

 36 omega -119.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -77.0000   30.0000 112

 37 omega  -70.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631   57.0000   30.0000 103

 38 omega -119.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -77.0000  -90.0000 112

 39 omega    7.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   77.0000  120.0000 112

 40 omega   11.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   57.0000 -150.0000 104

 41 omega    7.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   77.0000 -120.0000 112

 42 omega -157.00  -85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000    0.0000 72

 43 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 113

 44 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 113

 45 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 113

 46 omega -162.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 113

 47 omega -157.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000   90.0000 104

 48 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -120.0000 83

 49 omega   24.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -180.0000 85

 50 omega   78.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  120.0000 80

 51 omega   24.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -30.0000 85

 52 omega   75.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -150.0000 83

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0926327
_diffrn_orient_matrix_UB_12      -0.1118374
_diffrn_orient_matrix_UB_13      0.0781345
_diffrn_orient_matrix_UB_21      -0.1003751
_diffrn_orient_matrix_UB_22      0.0625114
_diffrn_orient_matrix_UB_23      0.0828305
_diffrn_orient_matrix_UB_31      -0.0964686
_diffrn_orient_matrix_UB_32      -0.1725328
_diffrn_orient_matrix_UB_33      -0.0206799
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17228
_diffrn_reflns_theta_full        72.39
_diffrn_reflns_theta_max         72.39
_diffrn_reflns_theta_min         3.32
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.4512
_exptl_crystal_size_mid          0.3172
_exptl_crystal_size_min          0.0558
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (98%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=0.08(4), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                3416
_reflns_number_total             3470
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5cc09329e2.cif
_cod_data_source_block           ed082
_cod_depositor_comments          'Adding full bibliography for 7118347.cif.'
_cod_database_code               7118347