Nickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique Cycloaddition of α,β-Unsaturated Phenyl Esters with Alkynes
Masato Ohashi; Tomoaki Taniguchi; Sensuke Ogoshi; Journal of the American Chemical Society 133 (2011) 14900–14903; doi:10.1021/ja2059999

data_4106820
_publ_section_title
;
 Nickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique
 Cycloaddition of \a,\b-Unsaturated Phenyl Esters with Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14900
_journal_page_last               14903
_journal_paper_doi               10.1021/ja2059999
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C51 H78 Ni O2 P2 '
_chemical_formula_sum            'C51 H78 Ni O2 P2'
_chemical_formula_weight         843.78
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.150(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9259(12)
_cell_length_b                   18.0957(14)
_cell_length_c                   18.4593(17)
_cell_measurement_reflns_used    18552
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      3.1
_cell_volume                     4651.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35722
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_correction_T_min  0.8587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.524
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         8168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0610
_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^)+(0.0440P)^2^+9.7076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                6270
_reflns_number_total             8168
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2059999_si_001_2.cif
_cod_data_source_block           bis-PCy3-Ni-PhCi
_cod_database_code               4106820