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_4025969
_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            'C22 H23 Cl O5'
_chemical_formula_weight         402.85
_chemical_name_systematic
; 
 Diethyl 2-(1-benzoyl-2-chloro-2-phenylethyl)malonate 
;
_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                109.9200(10)
_cell_angle_beta                 101.435(2)
_cell_angle_gamma                102.394(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2997(11)
_cell_length_b                   11.2333(14)
_cell_length_c                   11.4700(14)
_cell_measurement_temperature    293(2)
_cell_volume                     1051.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8924
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.780249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      3.224
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                3205
_reflns_number_total             4666
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1020773_si_005.cif
_cod_data_source_block           100118a_0m
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025969