Palladium Acetate-Catalyzed Cyclization Reaction of 2,3-Allenoic Acids in the Presence of Simple Allenes: An Efficient Synthesis of 4-(1'-Bromoalk-2'(Z)-en-2'-yl)furan-2(5H)-one Derivatives and the Synthetic Application
Zhenhua Gu; Xinke Wang; Wei Shu; Shengming Ma; Journal of the American Chemical Society 129 (2007) 10948–10956; doi:10.1021/ja072790j

data_4109861
_publ_section_title
;
 Palladium Acetate-Catalyzed Cyclization Reaction of 2,3-Allenoic Acids in
 the Presence of Simple Allenes: An Efficient Synthesis of
 4-(1'-Bromoalk-2'(Z)-en-2'-yl)furan-2(5H)-one Derivatives and the
 Synthetic Application
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10948
_journal_page_last               10956
_journal_paper_doi               10.1021/ja072790j
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C22 H23 Br O2'
_chemical_formula_weight         399.31
_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                 106.790(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3128(18)
_cell_length_b                   8.8210(13)
_cell_length_c                   18.775(3)
_cell_measurement_reflns_used    1707
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.389
_cell_measurement_theta_min      4.841
_cell_volume                     1952.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1412
_diffrn_reflns_av_sigmaI/netI    0.1522
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11159
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58765
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.502
_exptl_crystal_size_min          0.457
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.062(5)
_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   0.834
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.148
_refine_ls_shift/su_mean         0.083
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1197P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.2226
_reflns_number_gt                1623
_reflns_number_total             4229
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja072790jsi20070622_101802.cif
_cod_data_source_block           cd26125
_cod_database_code               4109861