Highly efficient and expedient synthesis of 5-hydroxy-1H-pyrrol-2-(5H)-ones from FeCl3-catalyzed tandem intramolecular enaminic addition of tertiary enamides to ketones and 1,3-hydroxy rearrangement.
Yang, Luo; Lei, Chuan-Hu; Wang, De-Xian; Huang, Zhi-Tang; Wang, Mei-Xiang; Organic letters 12 (2010) 3918–3921; doi:10.1021/ol101607z

data_1503169
_publ_section_title
;
 Highly efficient and expedient synthesis of
 5-hydroxy-1H-pyrrol-2-(5H)-ones from FeCl3-catalyzed tandem
 intramolecular enaminic addition of tertiary enamides to ketones and
 1,3-hydroxy rearrangement.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3918
_journal_page_last               3921
_journal_paper_doi               10.1021/ol101607z
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_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                110.89(3)
_cell_angle_beta                 95.92(3)
_cell_angle_gamma                99.62(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0436(16)
_cell_length_b                   10.604(2)
_cell_length_c                   11.289(2)
_cell_measurement_reflns_used    5492
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.96
_cell_volume                     873.0(4)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5492
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.359
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0702P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                2644
_reflns_number_total             3082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101607z_si_001.cif
_cod_data_source_block           a
_cod_original_cell_volume        873.0(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1503169