Chemodivergent synthesis of <i>cis</i>-4-hydroxyprolines from diastereomerically enriched epoxides.
DaSilva, Clement; Mauk, Grace; Forshee, Lucas; Pope, Oliver; Doherty, Mathilde; Ongbongan, Max; Lutz, Nicholas; Kamanya, Zemirah; Bhatt, Kara Chris; Braham, Andrew; Kubek, Miranda; Hawthorne, Summer; Campillo-Alvarado, Gonzalo; Bhattacharjee, Avik; Bowring, Miriam A.; O'Brien, Robert V; Organic & biomolecular chemistry 23 (2025) 4616–4621; doi:10.1039/d4ob01815j

data_7160347
_publ_section_title
;
 Chemodivergent synthesis of <i>cis</i>-4-hydroxyprolines from
 diastereomerically enriched epoxides.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4616
_journal_page_last               4621
_journal_paper_doi               10.1039/d4ob01815j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H23 N O5 S'
_chemical_formula_sum            'C16 H23 N O5 S'
_chemical_formula_weight         341.41
_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   geom
_audit_creation_date             2024-08-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-19 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.818(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4892(3)
_cell_length_b                   12.0747(5)
_cell_length_c                   18.9252(10)
_cell_measurement_reflns_used    3561
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      30.4380
_cell_measurement_theta_min      2.1670
_cell_volume                     1691.17(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      8.00  33.00   0.50   45.00    --   20.00  54.00 120.00   50
  2  \w    -71.00 107.00   0.50   45.00    --   20.00  54.00  30.00  356
  3  \w    -64.00  29.00   0.50   45.00    --   20.00  54.00 -30.00  186
  4  \w     59.00 105.00   0.50   45.00    --   20.00  54.00 -30.00   92
  5  \w    -13.00  13.00   0.50   45.00    --   20.00  54.00 -60.00   52
  6  \w    -73.00 -29.00   0.50   45.00    --   20.00  54.00-180.00   88
  7  \w      5.00  30.00   0.50   45.00    --   20.00  54.00-180.00   50
  8  \w     83.00 108.00   0.50   45.00    --   20.00  54.00-180.00   50
  9  \w    -66.00 -41.00   0.50   45.00    --   20.00  54.00 120.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.178
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.055
_refine_diff_density_max         1.430
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0983P)^2^+0.8826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2231
_reflns_number_total             2963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01815j2.cif
_cod_data_source_block           rvo_01092024_autored
_cod_depositor_comments
'Adding full bibliography for 7160347--7160350.cif.'
_cod_database_code               7160347
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
1.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B)
1.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C6(H6), C7(H7)
1.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C)
1.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_shelx_res_checksum              80579
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;