Copper-Catalyzed Intramolecular Alkene Carboetherification: Synthesis of Fused-Ring and Bridged-Ring Tetrahydrofurans
Yan Miller; Lei Miao; Azade S. Hosseini; Sherry R. Chemler; Journal of the American Chemical Society 134 (2012) 12149–12156; doi:10.1021/ja3034075

data_4118293
_publ_section_title
;
 Copper-Catalyzed Intramolecular Alkene Carboetherification: Synthesis of
 Fused-Ring and Bridged-Ring Tetrahydrofurans
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12149
_journal_page_last               12156
_journal_paper_doi               10.1021/ja3034075
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C31 H26 Cl2 O'
_chemical_formula_sum            'C31 H26 Cl2 O'
_chemical_formula_weight         485.42
_chemical_name_common            ubsc12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.452(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.425(3)
_cell_length_b                   10.6700(15)
_cell_length_c                   25.538(4)
_cell_measurement_reflns_used    4058
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.23
_cell_volume                     4959.5(13)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_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  0.1148
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            92319
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_correction_T_min  0.8997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       needle
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     769
_refine_ls_number_reflns         12314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+2.0728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                7868
_reflns_number_total             12314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3034075_si_002.cif
_cod_data_source_block           ubsc12
_cod_original_cell_volume        4959.7(12)
_cod_database_code               4118293