Palladium(0)-catalyzed [2+2+1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of terahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers
Diao, Yunxia; Zuo, Zhijun; Wang, Hui; Liu, Jingjing; Luan, Xinjun; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00768J

data_7155616
_publ_section_title
;
 Palladium(0)-catalyzed [2+2+1] cyclization of 1,6-enynes with vinyl
 bromides: a highly diastereoselective synthesis of
 terahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00768J
_journal_year                    2017
_chemical_formula_sum            'C23 H24 O'
_chemical_formula_weight         316.42
_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
_audit_update_record
;
2017-02-11 deposited with the CCDC.
2017-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                62.684(4)
_cell_angle_beta                 78.845(4)
_cell_angle_gamma                62.833(3)
_cell_formula_units_Z            2
_cell_length_a                   9.968(2)
_cell_length_b                   10.431(3)
_cell_length_c                   10.921(3)
_cell_measurement_reflns_used    1313
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      2.42
_cell_volume                     897.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4521
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0677P)^2^+0.0843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                2215
_reflns_number_total             3158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob00768j2.cif
_cod_data_source_block           xb9248_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7155616