Ruthenium/TFA-Catalyzed Coupling of Activated Secondary Propargylic Alcohols with Cyclic 1,3-Diones: Furan versus Pyran Ring Formation
Victorio Cadierno; Josefina Díez; José Gimeno; Noel Nebra; Journal of Organic Chemistry 73 (2008) 5852–5858; doi:10.1021/jo800726u

data_4023580
_publ_contact_author
;     Josefina D\'iez
      Departamento de Qu\'imica Org\'anica e Inorg\'anica
      Facultad de Qu\'imica
      Universidad de Oviedo
      Avda. Juli\'an Claver\'ia, 8
      33071 Oviedo
      Spain
;
_publ_contact_author_email       jdv@uniovi.es
_publ_contact_author_fax         '0034 98 5103446'
_publ_contact_author_phone       '0034 98 5102960'
_publ_section_title
;
 Ruthenium/TFA-Catalyzed Coupling of Activated Secondary Propargylic
 Alcohols with Cyclic 1,3-Diones: Furan versus Pyran Ring Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5852
_journal_page_last               5858
_journal_paper_doi               10.1021/jo800726u
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C12 H10 O2 S'
_chemical_formula_sum            'C12 H10 O2 S'
_chemical_formula_weight         218.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 100.571(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9439(4)
_cell_length_b                   6.1791(3)
_cell_length_c                   17.0548(7)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      0.407
_cell_volume                     1030.14(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowki & Minor 1997)'
_computing_data_collection       'Collet (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2007)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 92 (Altomare A., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95 mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\f and \w scan'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12603
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  1.035
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0538
_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^)+(0.1308P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1952
_reflns_number_gt                1267
_reflns_number_total             1849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800726u-File001_2.cif
_cod_data_source_block           13j
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023580