Synthesis of 4-hydroxypiperidines containing a quaternary stereocenter by aza-Prins cyclization.
Le Roch, Myriam; Gouault, Nicolas; Renault, Jacques; Argouarch, Gilles; Roisnel, Thierry; Banik, Swarnayu; Subba Reddy, B. V.; Lalli, Claudia; Organic & biomolecular chemistry 23 (2025) 1644–1652; doi:10.1039/d4ob01807a

data_7160323
_publ_section_title
;
 Synthesis of 4-hydroxypiperidines containing a quaternary stereocenter by
 aza-Prins cyclization.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1644
_journal_page_last               1652
_journal_paper_doi               10.1039/d4ob01807a
_journal_volume                  23
_journal_year                    2025
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C26 H27 N O5 S'
_chemical_formula_sum            'C26 H27 N O5 S'
_chemical_formula_weight         465.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_update_record
;
2024-10-16 deposited with the CCDC.	2024-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.221(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7842(13)
_cell_length_b                   10.2201(11)
_cell_length_c                   19.200(2)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4616
_cell_measurement_theta_min      2.2583
_cell_measurement_wavelength     0.710730
_cell_volume                     2308.7(4)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2023)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0483807
_diffrn_orient_matrix_UB_12      -0.0018334
_diffrn_orient_matrix_UB_13      -0.0411430
_diffrn_orient_matrix_UB_21      -0.0238807
_diffrn_orient_matrix_UB_22      -0.0923656
_diffrn_orient_matrix_UB_23      -0.0098371
_diffrn_orient_matrix_UB_31      -0.0656734
_diffrn_orient_matrix_UB_32      0.0322361
_diffrn_orient_matrix_UB_33      -0.0305260
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26305
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.125
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+1.1354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                4824
_reflns_number_total             5288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob01807a2.cif
_cod_data_source_block           JR1944_2
_cod_depositor_comments          'Adding full bibliography for 7160323.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160323
_shelx_res_checksum              36207