AlCl3-Promoted Highly Regio- and Diastereoselective [3 + 2] Cycloadditions of Activated Cyclopropanes and Aromatic Aldehydes: Construction of 2,5-Diaryl-3,3,4-trisubstituted Tetrahydrofurans
Gaosheng Yang; Yue Shen; Kui Li; Yongxian Sun; Yuanyuan Hua; Journal of Organic Chemistry 76 (2011) 229–233; doi:10.1021/jo1020773

data_4025966
_publ_section_title
;
 AlCl3-Promoted Highly Regio- and Diastereoselective [3 + 2]
 Cycloadditions of Activated Cyclopropanes and Aromatic Aldehydes:
 Construction of 2,5-Diaryl-3,3,4-trisubstituted Tetrahydrofurans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              229
_journal_page_last               233
_journal_paper_doi               10.1021/jo1020773
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C29 H28 O6'
_chemical_formula_weight         472.51
_chemical_name_systematic
; 
 Diethyl r-4-benzoyl-c-2,c-5-diphenyltetrahydrofuran-3,3-dicarboxylate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.840(8)
_cell_angle_beta                 90.489(8)
_cell_angle_gamma                92.944(8)
_cell_formula_units_Z            4
_cell_length_a                   10.529(7)
_cell_length_b                   15.041(10)
_cell_length_c                   17.359(12)
_cell_measurement_temperature    293(2)
_cell_volume                     2547(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.1128
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18454
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.479979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         9647
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.2140
_refine_ls_R_factor_gt           0.1279
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3492
_refine_ls_wR_factor_ref         0.4020
_reflns_number_gt                4530
_reflns_number_total             9647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1020773_si_002.cif
_cod_data_source_block           090421a_0m
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C58 H56 O12'
_cod_original_formula_weight         945.03
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025966