Brønsted-base-catalyzed Remote Cascade Reactivity of 2,4-Dienones - Asymmetric Synthesis of Tetrahydrothiophenes
Przydacz, Artur; Kowalczyk, Rafał; Albrecht, Lukasz; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02397A

data_7155913
_publ_section_title
;
 Br\/onsted-base-catalyzed Remote Cascade Reactivity of 2,4-Dienones -
 Asymmetric Synthesis of Tetrahydrothiophenes
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02397A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H22 O4 S'
_chemical_formula_sum            'C23 H22 O4 S'
_chemical_formula_weight         394.46
_chemical_name_systematic
'Phenyl 4-hydroxy-3-(3-oxocyclohex-1-en-1-yl)-4-phenyltetrahydrothiophene-2-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-05-10 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                84.0710(10)
_cell_angle_beta                 82.0360(10)
_cell_angle_gamma                83.6930(10)
_cell_formula_units_Z            1
_cell_length_a                   5.6715(2)
_cell_length_b                   8.7531(2)
_cell_length_c                   10.1807(2)
_cell_measurement_reflns_used    382
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.4559
_cell_measurement_theta_min      8.7879
_cell_volume                     495.50(2)
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_collection       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5975
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.732
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         84.600
_diffrn_reflns_theta_min         4.403
_diffrn_source                   'sealed X-ray microsource'
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+0.2735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.721
_reflns_Friedel_fraction_max     0.605
_reflns_number_gt                3241
_reflns_number_total             3276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02397a2.cif
_cod_data_source_block           la_ap_320a_a
_cod_database_code               7155913
_shelx_shelxl_version_number     2014/7
_d_diffrn_detector_area_resol_mean 8.3333
_shelx_res_checksum              9493