Diastereoselective synthesis of 2-arylmethylene-6-hydroxyspiro[4.5]deca-7-ones via FeCl3·6H2O-catalyzed spiroannulation/hydride transfer of 6-(5-arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols.
Lin, Hsin-Hui; Lee, Kuan-Yi; Chen, Yin-An; Liu, Chi-Fan; Yeh, Ming-Chang P; The Journal of organic chemistry 79 (2014) 11802–11811; doi:10.1021/jo5023266

data_4030215
_publ_section_title
;
 Diastereoselective synthesis of
 2-arylmethylene-6-hydroxyspiro[4.5]deca-7-ones via
 FeCl3&#x00B7;6H2O-catalyzed spiroannulation/hydride transfer of
 6-(5-arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11802
_journal_page_last               11811
_journal_paper_doi               10.1021/jo5023266
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C23 H24 O2'
_chemical_formula_sum            'C23 H24 O2'
_chemical_formula_weight         332.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 99.946(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5496(7)
_cell_length_b                   7.1138(3)
_cell_length_c                   17.4167(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1775.59(15)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12190
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9441
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.74
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0889P)^2^+1.1465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1855
_reflns_number_gt                2445
_reflns_number_total             3130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5023266_si_005.cif
_cod_data_source_block           ch16273
_cod_depositor_comments
'Adding full bibliography for 4030212--4030218.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4030215