Diastereoselective construction of azabicyclo[3.1.0]hexan-2-ones <i>via</i> a base-mediated cascade annulation of β-oxo-acrylamides with vinylsulfonium salts.
Wang, Zhaoxue; Wu, Ping; Yan, Rui; Zhao, Zhen-Guo; Du, Yuhang; Xiao, Yilei; Wu, Lingang; Xie, Lei; Organic & biomolecular chemistry 23 (2025) 10285–10289; doi:10.1039/d5ob01439e

data_7160830
_publ_section_title
;
 Diastereoselective construction of azabicyclo[3.1.0]hexan-2-ones
 <i>via</i> a base-mediated cascade annulation of &#x3b2;-oxo-acrylamides
 with vinylsulfonium salts.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10285
_journal_page_last               10289
_journal_paper_doi               10.1039/d5ob01439e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C26 H23 N O3'
_chemical_formula_sum            'C26 H23 N O3'
_chemical_formula_weight         397.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-22
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2025-05-04 deposited with the CCDC.	2025-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.2520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1530(3)
_cell_length_b                   6.2741(2)
_cell_length_c                   15.0812(4)
_cell_measurement_reflns_used    6594
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      67.665
_cell_measurement_theta_min      5.423
_cell_volume                     1038.46(5)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13453
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.101
_diffrn_reflns_theta_min         4.028
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6429
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1488 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.8538.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0473P)^2^+0.0499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                3270
_reflns_number_total             3529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01439e2.cif
_cod_data_source_block           xl
_cod_depositor_comments          'Adding full bibliography for 7160830.cif.'
_cod_database_code               7160830
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.901
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C23(H23), C24(H24), C27(H27)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              9575
_olex2_submission_special_instructions 'No special instructions were received'