PdCl2-Catalyzed Two-Component Cross-Coupling Cyclization of 2,3-Allenoic Acids with 2,3-Allenols. An Efficient Synthesis of 4-(1',3'-Dien-2'-yl)-2(5H)-furanone Derivatives
Shengming Ma; Zhenhua Gu; Journal of the American Chemical Society 127 (2005) 6182–6183; doi:10.1021/ja0500815

data_4111651
_publ_section_title
;
 PdCl2-Catalyzed Two-Component Cross-Coupling Cyclization of 2,3-Allenoic
 Acids with 2,3-Allenols. An Efficient Synthesis of
 4-(1',3'-Dien-2'-yl)-2(5H)-furanone Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6182
_journal_page_last               6183
_journal_paper_doi               10.1021/ja0500815
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C19 H26 O2'
_chemical_formula_weight         286.40
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 97.363(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.423(3)
_cell_length_b                   6.5858(8)
_cell_length_c                   17.641(2)
_cell_measurement_reflns_used    2312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.604
_cell_measurement_theta_min      4.656
_cell_volume                     3275.0(6)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9178
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53641
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.409
_exptl_crystal_size_min          0.327
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0007(4)
_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   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0739P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                2482
_reflns_number_total             3565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0500815si20050106_093336.cif
_cod_data_source_block           cd24440
_cod_original_cell_volume        3275.0(7)
_cod_database_code               4111651