cis-2,3-Disubstituted Cyclopropane 1,1-Diesters in [3 + 2] Annulations with Aldehydes: Highly Diastereoselective Construction of Densely Substituted Tetrahydrofurans
Gaosheng Yang; Yongxian Sun; Yue Shen; Zhuo Chai; Shuangliu Zhou; Jiang Chu; Jun Chai; Journal of Organic Chemistry 78 (2013) 5393–5400; doi:10.1021/jo400554a

data_4028283
_publ_section_title
;
 cis-2,3-Disubstituted Cyclopropane 1,1-Diesters in [3 + 2] Annulations
 with Aldehydes: Highly Diastereoselective Construction of Densely
 Substituted Tetrahydrofurans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5393
_journal_page_last               5400
_journal_paper_doi               10.1021/jo400554a
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C29 H26 Cl2 O6'
_chemical_formula_weight         541.40
_chemical_name_systematic
; 
 Diethyl r-4-benzoyl-t-2-(2,4-dichlorophenyl)-t-5-phenyltetrahydrofuran
-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                69.581(2)
_cell_angle_beta                 87.931(2)
_cell_angle_gamma                77.008(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3298(11)
_cell_length_b                   11.5891(15)
_cell_length_c                   15.560(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1370.2(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 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11796
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.277
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1145P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.2130
_reflns_number_gt                4084
_reflns_number_total             6154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400554a_si_002.cif
_cod_data_source_block           100519a_0m
_cod_database_code               4028283