Phosphine-Catalyzed Annulation Reactions of 2-Butynoate and α-Keto Esters: Synthesis of Cyclopentene Derivatives
Mbofana, Curren T.; Miller, Scott J.; ACS Catalysis 4 (2014) 3671–; doi:10.1021/cs501117h

data_4511980
_publ_section_title
;
 Phosphine-Catalyzed Annulation Reactions of 2-Butynoate and \a-Keto
 Esters: Synthesis of Cyclopentene Derivatives
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              3671
_journal_paper_doi               10.1021/cs501117h
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C18 H16 O6'
_chemical_formula_weight         328.31
_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                72.370(5)
_cell_angle_beta                 89.090(6)
_cell_angle_gamma                66.272(5)
_cell_formula_units_Z            4
_cell_length_a                   10.2090(2)
_cell_length_b                   11.5382(2)
_cell_length_c                   15.2590(11)
_cell_measurement_reflns_used    25110
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      67.8
_cell_measurement_theta_min      7.2
_cell_volume                     1556.57(15)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47179
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_min         7.21
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  0.9570
_exptl_absorpt_correction_T_min  0.8784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0481P)^2^+0.4826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                4949
_reflns_number_total             5473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs501117h_si_002.cif
_cod_data_source_block           12054
_cod_depositor_comments          'Adding full bibliography for 4511980.cif.'
_cod_original_cell_volume        1556.57(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511980