A concise and highly diastereoselective one-pot synthesis of vicinal tetrasubstituted furofuran analogues
Sneka, Chinnaiyah; Manikandan, Balasubramaniyam; Thamotharan, Subbiah; Blacque, Olivier; Selva Ganesan, Subramaniapillai; New Journal of Chemistry 49 (2025) 11297–11303; doi:10.1039/D5NJ01435B

data_7063855
_publ_section_title
;
 A concise and highly diastereoselective one-pot synthesis of vicinal
 tetrasubstituted furofuran analogues
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11297
_journal_page_last               11303
_journal_paper_doi               10.1039/D5NJ01435B
_journal_volume                  49
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 N2 O6'
_chemical_formula_sum            'C18 H16 N2 O6'
_chemical_formula_weight         356.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-12
_audit_creation_method
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_audit_update_record
;
2025-03-16 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.134(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2247(2)
_cell_length_b                   9.2088(1)
_cell_length_c                   14.6416(2)
_cell_measurement_reflns_used    14627
_cell_measurement_temperature    160.0(1)
_cell_measurement_theta_max      76.3730
_cell_measurement_theta_min      4.3870
_cell_volume                     1631.69(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.97a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.97a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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   -117.00 -15.00   1.00    1.00    --  -41.01 -36.00-146.00  102
  2  \w   -117.00 -15.00   1.00    1.00    --  -41.01 -36.00-146.00  102
  3  \w     15.00 117.00   1.00    1.00    --   41.01  36.00  10.00  102
  4  \w    -35.00  67.00   1.00    1.00    --   41.01 -36.00-146.00  102
  5  \w     87.00 178.00   1.00    1.50    --  113.00  36.00  10.00   91
  6  \w     37.00 139.00   1.00    1.50    --  113.00 -36.00-146.00  102
  7  \w    -67.00  35.00   1.00    1.00    --  -41.01  36.00  10.00  102
  8  \w    -87.00 -20.00   1.00    1.00    --  -41.01 125.00  60.00   67
  9  \w     27.00  96.00   1.00    1.00    --   41.01-125.00  60.00   69
 10  \w     12.00  38.00   1.00    1.00    --   41.01  52.00   1.06   26
 11  \w     12.00  38.00   1.00    1.00    --   41.01  52.00 -99.92   26
 12  \w     13.00  43.00   1.00    1.00    --   41.01  49.00 128.71   30
 13  \w     13.00  43.00   1.00    1.00    --   41.01  49.00-128.67   30
 14  \w     12.00  39.00   1.00    1.00    --   41.01  51.00  43.33   27
 15  \w     16.00  50.00   1.00    1.00    --   44.00  46.00  91.21   34
 16  \w     61.00 165.00   1.00    1.50    --   88.00  34.00 -52.21  104
 17  \w     61.00 165.00   1.00    1.50    --   88.00  34.00 -52.21  104
 18  \w     82.00 178.00   1.00    1.50    --  113.00  30.00 -30.00   96
 19  \w     61.00 146.00   1.00    1.50    --  113.00 178.00 120.00   85
 20  \w     38.00 109.00   1.00    1.50    --  113.00-111.00-180.00   71
 21  \w    115.00 178.00   1.00    1.50    --  113.00  77.00 -90.00   63
 22  \w     38.00 109.00   1.00    1.50    --  113.00-111.00   0.00   71
 23  \w    113.00 178.00   1.00    1.50    --  113.00  61.00-120.00   65
 24  \w     61.00 146.00   1.00    1.50    --  113.00 178.00 150.00   85
 25  \w     38.00 109.00   1.00    1.50    --  113.00-111.00 -30.00   71
 26  \w    113.00 178.00   1.00    1.50    --  113.00  61.00 -30.00   65
 27  \w     38.00 109.00   1.00    1.50    --  113.00-111.00-150.00   71
 28  \w     38.00 109.00   1.00    1.50    --  113.00-111.00 120.00   71
 29  \w     38.00 109.00   1.00    1.50    --  113.00-111.00 120.00   71
 30  \w     39.00 143.00   1.00    1.50    --  113.00 -61.00 120.00  104
 31  \w     82.00 178.00   1.00    1.50    --  113.00  30.00-150.00   96
 32  \w     82.00 178.00   1.00    1.50    --  113.00  30.00 -30.00   96
 33  \w     97.00 178.00   1.00    1.50    --  113.00  45.00 150.00   81
 34  \w    105.00 178.00   1.00    1.50    --  113.00 111.00 -30.00   73
 35  \w     38.00 109.00   1.00    1.50    --  113.00-111.00  30.00   71
 36  \w     38.00 109.00   1.00    1.50    --  113.00-111.00 -90.00   71
 37  \w     38.00 109.00   1.00    1.50    --  113.00-111.00  90.00   71
 38  \w    113.00 178.00   1.00    1.50    --  113.00  61.00 -60.00   65
 39  \w     29.00 107.00   1.00    1.50    --  113.00 -94.00 120.00   78
 40  \w     -3.00  24.00   1.00    1.00    --   28.00  62.00 145.02   27
 41  \w      2.00  28.00   1.00    1.00    --   32.00  59.00  70.38   26
 42  \w     12.00  38.00   1.00    1.00    --   41.01  52.00 -16.96   26
 43  \w     27.00  96.00   1.00    1.00    --   41.01-125.00-150.00   69
 44  \w     12.00  39.00   1.00    1.00    --   41.01  51.00-173.75   27
 45  \w     12.00  39.00   1.00    1.00    --   41.01  51.00 142.09   27
 46  \w     16.00  50.00   1.00    1.00    --   44.00  46.00 -58.39   34
 47  \w     22.00 124.00   1.00    1.00    --   48.00  38.00 158.37  102
 48  \w     31.00 138.00   1.00    1.00    --   60.00  31.00-120.65  107
 49  \w     34.00 136.00   1.00    1.00    --   60.00  37.00-170.54  102
 50  \w    -40.00 -15.00   1.00    1.00    --  -41.01  36.00  10.00   25
 51  \w    108.00 133.00   1.00    1.50    --  113.00  36.00   9.00   25
 52  \w    128.00 177.00   1.00    1.50    --  113.00 111.00  30.00   49
 53  \w     42.00  67.00   1.00    1.00    --   41.01  36.00   9.00   25
 54  \w     -7.00  21.00   1.00    1.00    --   24.00  65.00   3.14   28
 55  \w     -7.00  21.00   1.00    1.00    --   24.00  65.00  92.73   28
 56  \w     -3.00  24.00   1.00    1.00    --   28.00  62.00 -92.33   27
 57  \w     -2.00  25.00   1.00    1.00    --   28.00  61.00 -57.77   27
 58  \w      2.00  28.00   1.00    1.00    --   32.00  59.00-155.97   26
 59  \w     20.00  48.00   1.00    1.00    --   48.00  47.00 159.92   28
 60  \w     24.00 129.00   1.00    1.00    --   52.00  32.00 131.24  105
 61  \w     33.00 137.00   1.00    1.00    --   60.00  33.00  44.59  104
 62  \w     41.00 143.00   1.00    1.00    --   68.00  40.00 -96.84  102
 63  \w     49.00 152.00   1.00    1.00    --   76.00  39.00 -93.99  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0897904000
_diffrn_orient_matrix_UB_12      -0.1095389000
_diffrn_orient_matrix_UB_13      -0.0179579000
_diffrn_orient_matrix_UB_21      0.0900562000
_diffrn_orient_matrix_UB_22      0.1048306000
_diffrn_orient_matrix_UB_23      0.0451376000
_diffrn_orient_matrix_UB_31      -0.0057558000
_diffrn_orient_matrix_UB_32      -0.0707233000
_diffrn_orient_matrix_UB_33      0.0945235000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19613
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_min         4.416
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.97a (Rigaku Oxford Diffraction, 2023)
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            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       irregular
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0432P)^2^+0.2345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0684
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3213
_reflns_number_total             3338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj01435b2.cif
_cod_data_source_block           tham0901
_cod_depositor_comments          'Adding full bibliography for 7063855.cif.'
_cod_database_code               7063855
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.814
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_shelx_res_checksum              974