Facile synthesis of multisubstituted 2,3-dihydrofurans <i>via</i> intermolecular cyclization of enals or alkyl/aryl aldehydes with acyl-stabilized sulfur ylides.
Su, Yin; Sun, Ziyi; Zhao, Quansheng; Fu, Liang; Chemical communications (Cambridge, England) 62 (2026) 2585–2588; doi:10.1039/d5cc06219e

data_7135485
_publ_section_title
;
 Facile synthesis of multisubstituted 2,3-dihydrofurans <i>via</i>
 intermolecular cyclization of enals or alkyl/aryl aldehydes with
 acyl-stabilized sulfur ylides.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2585
_journal_page_last               2588
_journal_paper_doi               10.1039/d5cc06219e
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H21 N O4 S'
_chemical_formula_sum            'C27 H21 N O4 S'
_chemical_formula_weight         455.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2mkvjl
_audit_creation_date             2023-11-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-03-10 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0438(14)
_cell_length_b                   20.1986(17)
_cell_length_c                   14.2693(13)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.716
_cell_measurement_theta_min      2.778
_cell_volume                     4624.1(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      296.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1444
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            237933
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.176
_diffrn_reflns_theta_max         25.176
_diffrn_reflns_theta_min         2.732
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0867 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.9066.
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    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_recrystallization_method
'The crystals were growth by means of evaporation of a mixture of n-hexane and toluene at RT.'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         8223
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0474P)^2^+1.5335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1187
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5979
_reflns_number_total             8223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06219e2.cif
_cod_data_source_block           20231124c
_cod_database_code               7135485
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.974
_exptl_crystal_mounting_method
'Crystals were removed from the crystallisation vial and immediately coated with polybutenes oil (CAS: 9003-29-6) on a glass slide. A suitable single crystal coated with polybutenes oil as less as possible was sealed in capillary tube filled with argon. The capillary tube with single crystal was mounted on copper pin with solid paraffin.'
_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. Uiso/Uaniso restraints and constraints
C48 \\sim O8 \\sim C49 \\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim
O8A \\sim C49A \\sim C50A \\sim C51A \\sim C52A \\sim C53A \\sim C54A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Same fragment restrains
{C48, O8A, C49A, C50A, C51A, C52A, C53A, C54A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C48, O8, C49, C50, C51, C52, C53, C54}
4. Others
 Sof(O8A)=Sof(C49A)=Sof(C50A)=Sof(H50A)=Sof(C51A)=Sof(H51A)=Sof(C52A)=
 Sof(H52A)=Sof(C53A)=Sof(H53A)=Sof(C54A)=Sof(H54A)=1-FVAR(1)
 Sof(O8)=Sof(C49)=Sof(C50)=Sof(H50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=
 Sof(C53)=Sof(H53)=Sof(C54)=Sof(H54)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C30(H30), C31(H31)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C39(H39A,H39B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C33(H33), C34(H34),
  C35(H35), C36(H36), C37(H37), C42(H42), C43(H43), C44(H44), C45(H45),
 C50(H50), C51(H51), C52(H52), C53(H53), C54(H54), C50A(H50A), C51A(H51A),
 C52A(H52A), C53A(H53A), C54A(H54A)
5.d Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10), C22(C23,C24,C25,C26,C27), C32(C33,C34,C35,C36,C37),
 C49(C50,C51,C52,C53,C54), C49A(C50A,C51A,C52A,C53A,C54A)
5.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              85249
_shelx_hkl_checksum              59769
_olex2_submission_special_instructions 'No special instructions were received'