Regio- and stereoselective synthesis of 2-cyclopentenones via a hydrogenolysis-terminated Heck cyclization of β-alkylthio dienones.
Liu, Bangyu; Zheng, Gang; Liu, Xiaocui; Xu, Cong; Liu, Jingxin; Wang, Mang; Chemical Communications (Cambridge, United Kingdom) 49 (2013) 2201–2203; doi:10.1039/c3cc37571d

data_7108916
_publ_section_title
;
 Regio- and stereoselective synthesis of 2-cyclopentenones via a
 hydrogenolysis-terminated Heck cyclization of \b-alkylthio dienones.
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   22
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2201
_journal_page_last               2203
_journal_paper_doi               10.1039/c3cc37571d
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C20 H20 O2 S'
_chemical_formula_weight         324.42
_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                 107.291(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0155(8)
_cell_length_b                   8.2100(3)
_cell_length_c                   11.6450(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1735.83(13)
_computing_cell_refinement       CrysAlis
_computing_data_collection       'CrysAlis (Oxford Diffraction,2006)'
_computing_data_reduction        CrysAlis
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford diffraction Gemini R Ultra'
_diffrn_measurement_method       '\w scan'
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6642
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0501P)^2^+0.3350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                2397
_reflns_number_total             3048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc37571d.txt
_cod_data_source_block           w
_cod_original_cell_volume        1735.83(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7108916