Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by a Neighboring Carbonyl Group: Access to α-Acyloxy Methyl Ketones and Synthesis of (\±)-Actinopolymorphol B
Nayan Ghosh; Sanatan Nayak; Akhila K. Sahoo; Journal of Organic Chemistry 76 (2011) 500–511; doi:10.1021/jo101995g

data_4025987
_publ_section_title
;
 Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by
 a Neighboring Carbonyl Group: Access to \a-Acyloxy Methyl Ketones and
 Synthesis of (\+-)-Actinopolymorphol B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              500
_journal_page_last               511
_journal_paper_doi               10.1021/jo101995g
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C13 H16 O5'
_chemical_formula_sum            'C13 H16 O5'
_chemical_formula_weight         252.26
_chemical_name_common            '1-(2,6-dimethoxyphenyl)-2-oxopropyl acetate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 111.194(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9349(7)
_cell_length_b                   23.640(3)
_cell_length_c                   8.4832(9)
_cell_measurement_reflns_used    3884
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.58
_cell_measurement_theta_min      2.72
_cell_volume                     1296.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Phi and Omega 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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12327
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9727
_exptl_absorpt_correction_T_min  0.9428
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0613P)^2^+0.2868P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                1908
_reflns_number_total             2279
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101995g_si_003.cif
_cod_data_source_block           aks22_m
_cod_original_cell_volume        1296.7(2)
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4025987