Enantioselective Michael addition of 3-hydroxy-2-pyridone to nitroolefins using cinchona-derived bifunctional organocatalysts.
Gi, Minseok; Oh, Daehyun; Yang, Sehun; Lee, Jaeyong; Jung, So Hyun; Baek, Ju Ha; Ha, Min Woo; Lee, Geumwoo; Park, Hyeung-Geun; Organic & biomolecular chemistry 22 (2024) 7017–7023; doi:10.1039/d4ob01042f

data_7160096
_publ_section_title
;
 Enantioselective Michael addition of 3-hydroxy-2-pyridone to nitroolefins
 using cinchona-derived bifunctional organocatalysts.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7017
_journal_page_last               7023
_journal_paper_doi               10.1039/d4ob01042f
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 N2 O6 S'
_chemical_formula_sum            'C22 H22 N2 O6 S'
_chemical_formula_weight         442.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-07-30 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8856(10)
_cell_length_b                   13.443(2)
_cell_length_c                   26.710(5)
_cell_measurement_reflns_used    4405
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.74
_cell_volume                     2113.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1348
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            43950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_min         2.150
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
; 
 Flack x determined using 878 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5242
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1510
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0818P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1797
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2737
_reflns_number_total             5242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01042f2.cif
_cod_data_source_block           ODJ19_78_a
_cod_depositor_comments          'Adding full bibliography for 7160096.cif.'
_cod_database_code               7160096
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              25596