Mechanistic and Sterochemical Insights on the Pt-Catalyzed Rearrangement of Oxiranylpropargylic Esters to Cyclopentenones
Adán B. González-Pérez; Belén Vaz; Olalla Nieto Faza; Ángel R. de Lera; Journal of Organic Chemistry 77 (2012) 8733–8743; doi:10.1021/jo301651r

data_4027566
_publ_section_title
;
 Mechanistic and Sterochemical Insights on the Pt-Catalyzed Rearrangement
 of Oxiranylpropargylic Esters to Cyclopentenones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8733
_journal_page_last               8743
_journal_paper_doi               10.1021/jo301651r
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 97.438(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.579(2)
_cell_length_b                   8.691(3)
_cell_length_c                   12.535(5)
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.09
_cell_measurement_theta_min      2.86
_cell_volume                     710.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART1000 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5265
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0581P)^2^+0.1261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                1681
_reflns_number_total             2472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301651r_si_002.cif
_cod_data_source_block           ar07081s
_cod_original_cell_volume        710.8(5)
_cod_database_code               4027566