A Copper(II)-Mediated Regioselective Cyclization-Acetoxylation of 6,8-Dien-1-ones for the Synthesis of Functionalized Cyclopentanes
Yazhou Wang; Haifeng Du; Journal of Organic Chemistry 75 (2010) 3503–3506; doi:10.1021/jo100413p

data_4025431
_publ_section_title
;
 A Copper(II)-Mediated Regioselective Cyclization-Acetoxylation of
 6,8-Dien-1-ones for the Synthesis of Functionalized Cyclopentanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3503
_journal_page_last               3506
_journal_paper_doi               10.1021/jo100413p
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C22 H21 Br O3'
_chemical_formula_sum            'C22 H21 Br O3'
_chemical_formula_weight         413.29
_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                96.42(3)
_cell_angle_beta                 100.91(3)
_cell_angle_gamma                109.24(3)
_cell_formula_units_Z            4
_cell_length_a                   10.290(2)
_cell_length_b                   11.499(2)
_cell_length_c                   18.124(4)
_cell_measurement_reflns_used    659
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1952.7(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24028
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    2.123
_exptl_absorpt_correction_T_max  0.6761
_exptl_absorpt_correction_T_min  0.6189
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8895
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+1.4223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                7123
_reflns_number_total             8895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100413p_si_002.cif
_cod_data_source_block           sa218
_cod_original_cell_volume        1952.7(7)
_cod_database_code               4025431