Syntheses of 3,4-Disubstituted Pyrroles and Furans via Lewis Acid-Promoted Semipinacol Rearrangement/Alkyne-Ketone Metathesis Reaction of (C)-2-N- or O-((3-Arylpropargyl)methyl)-Tethered 3,5,5-Trimethyl-2,3-epoxycyclohexan-1-ones
Ming-Chang P. Yeh; Ming-Nan Lin; Ching-Hsien Hsu; Chia-Jung Liang; Journal of Organic Chemistry 78 (2013) 12381–12396; doi:10.1021/jo402025z

data_4028845
_publ_section_title
;
 Syntheses of 3,4-Disubstituted Pyrroles and Furans via Lewis
 Acid-Promoted Semipinacol Rearrangement/Alkyne-Ketone Metathesis Reaction
 of (C)-2-N- or O-((3-Arylpropargyl)methyl)-Tethered
 3,5,5-Trimethyl-2,3-epoxycyclohexan-1-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12381
_journal_page_last               12396
_journal_paper_doi               10.1021/jo402025z
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C17 H19 N O2 S1'
_chemical_formula_sum            'C17 H19 N O2 S'
_chemical_formula_weight         301.39
_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                 91.44(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.04(3)
_cell_length_b                   6.146(15)
_cell_length_c                   19.61(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1571(7)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.4149
_diffrn_reflns_av_sigmaI/netI    0.6933
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7464
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.8705
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.4288
_refine_ls_R_factor_gt           0.0991
_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^)+(0.1317P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2046
_refine_ls_wR_factor_ref         0.4030
_reflns_number_gt                553
_reflns_number_total             2794
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402025z_si_009.cif
_cod_data_source_block           ch14314
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028845