Organocatalytic enantioselective synthesis of 2,5,5-trisubstituted piperidines bearing a quaternary stereocenter. Vinyl sulfonamide as a new amine protecting group.
Escolano, Marcos; Guerola, Marta; Torres, Javier; Gaviña, Daniel; Alzuet-Piña, Gloria; Sánchez-Rosello, María; Del Pozo, Carlos; Chemical communications (Cambridge, England) 56 (2020) 1425–1428; doi:10.1039/c9cc09113k

data_7125692
_publ_section_title
;
 Organocatalytic enantioselective synthesis of 2,5,5-trisubstituted
 piperidines bearing a quaternary stereocenter. Vinyl sulfonamide as a new
 amine protecting group.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1425
_journal_page_last               1428
_journal_paper_doi               10.1039/c9cc09113k
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H24 N2 O5 S2'
_chemical_formula_sum            'C14 H24 N2 O5 S2'
_chemical_formula_weight         364.48
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-09T13:55:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-01-15 deposited with the CCDC.	2019-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4852(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.25874(8)
_cell_length_b                   6.61591(6)
_cell_length_c                   18.72215(18)
_cell_measurement_reflns_used    6625
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.28
_cell_measurement_theta_min      4.687
_cell_volume                     898.795(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -102.00 -61.00   1.00    1.00    --  -42.13-152.00   3.00   41
  2  \w   -121.00 -25.00   1.00    1.00    --  -42.13 -19.00  60.00   96
  3  \w     12.00  97.00   1.00    1.00    --   42.13-125.00-120.00   85
  4  \w     80.00 106.00   1.00    1.00    --   42.13 152.00  46.00   26
  5  \w    -25.00  60.00   1.00    1.00    --   42.13 -57.00   0.00   85
  6  \w     73.00 107.00   1.00    1.00    --  107.93 -94.00  60.00   34
  7  \w     27.00  67.00   1.00    1.00    --  107.93 -94.00  60.00   40
  8  \w     32.00 140.00   1.00    1.00    --  107.93 -77.00-120.00  108
  9  \w     35.00  61.00   1.00    1.00    --  107.93 -30.00-120.00   26
 10  \w     84.00 133.00   1.00    1.00    --  107.93  45.00  60.00   49
 11  \w     36.00  62.00   1.00    1.00    --  107.93 -30.00 120.00   26
 12  \w     98.00 147.00   1.00    1.00    --  107.93  45.00  90.00   49
 13  \w     40.00  70.00   1.00    1.00    --  107.93-125.00  60.00   30
 14  \w     79.00 112.00   1.00    1.00    --  107.93-125.00  60.00   33
 15  \w     36.00  67.00   1.00    1.00    --  107.93 -30.00-150.00   31
 16  \w     43.00 116.00   1.00    1.00    --  107.93-125.00-120.00   73
 17  \w     79.00 155.00   1.00    1.00    --  107.93  61.00-180.00   76
 18  \w    123.00 153.00   1.00    1.00    --  107.93  45.00 -90.00   30
 19  \w    126.00 157.00   1.00    1.00    --  107.93  97.00  -8.00   31
 20  \w     83.00 138.00   1.00    1.00    --  107.93 125.00  90.00   55
 21  \w     76.00 158.00   1.00    1.00    --  107.93 125.00-150.00   82
 22  \w    -80.00 -22.00   1.00    1.00    --  -42.13  19.00  90.00   58
 23  \w     39.00  68.00   1.00    1.00    --  107.93 -30.00  60.00   29
 24  \w     37.00  64.00   1.00    1.00    --  107.93 -30.00-180.00   27
 25  \w     69.00  96.00   1.00    1.00    --  107.93-125.00-180.00   27
 26  \w     99.00 157.00   1.00    1.00    --  107.93  77.00 -30.00   58
 27  \w     41.00  67.00   1.00    1.00    --  107.93 -45.00  90.00   26
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0067621
_diffrn_orient_matrix_UB_12      -0.1002634
_diffrn_orient_matrix_UB_13      -0.074161
_diffrn_orient_matrix_UB_21      -0.0772762
_diffrn_orient_matrix_UB_22      0.194557
_diffrn_orient_matrix_UB_23      -0.0346711
_diffrn_orient_matrix_UB_31      0.1976133
_diffrn_orient_matrix_UB_32      0.0794087
_diffrn_orient_matrix_UB_33      -0.0087125
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7162
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.949
_diffrn_reflns_theta_min         4.725
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.918
_exptl_absorpt_correction_T_max  0.819
_exptl_absorpt_correction_T_min  0.283
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.35
_exptl_crystal_description       prism
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.589
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1456 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (99%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=-0.001(6)
 
;
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.1130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0657
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3275
_reflns_number_total             3310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09113k2.cif
_cod_data_source_block           a20180275_mp2991
_cod_depositor_comments          'Adding full bibliography for 7125692.cif.'
_cod_original_cell_volume        898.795(16)
_cod_database_code               7125692