Diastereoselective tandem reactions of substituted 3-sulfolenes with bis-vinyl ketones leading to highly functionalized bicyclic and tricyclic frameworks.
Brant, Michael G.; Friedmann, Jordan N.; Bohlken, Connor G.; Oliver, Allen G.; Wulff, Jeremy E.; Organic & biomolecular chemistry 13 (2015) 4581–4588; doi:10.1039/c5ob00387c

data_7154362
_publ_section_title
;
 Diastereoselective tandem reactions of substituted 3-sulfolenes with
 bis-vinyl ketones leading to highly functionalized bicyclic and tricyclic
 frameworks.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4581
_journal_page_last               4588
_journal_paper_doi               10.1039/c5ob00387c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C24 H26 O5 S'
_chemical_formula_sum            'C24 H26 O5 S'
_chemical_formula_weight         426.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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   mixed
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2014-09-18 deposited with the CCDC.
2015-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                95.0350(14)
_cell_angle_beta                 95.5230(15)
_cell_angle_gamma                96.4600(15)
_cell_formula_units_Z            4
_cell_length_a                   9.7206(4)
_cell_length_b                   14.2444(5)
_cell_length_c                   15.3744(5)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.39
_cell_volume                     2094.98(13)
_computing_cell_refinement       'Bruker SAINT v8.32B'
_computing_data_collection       'Bruker APEX-II v2013-10.0'
_computing_data_reduction        'Bruker SAINT v8.32B'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of \w and \f-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  0.0420
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            48272
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.186
_diffrn_reflns_theta_min         1.337
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9462
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       rod
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         9304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+1.2101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7099
_reflns_number_total             9304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00387c2.cif
_cod_data_source_block           uvic1408a
_cod_depositor_comments
'Adding full bibliography for 7154360--7154364.cif.'
_cod_database_code               7154362
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2014-3
_shelx_res_checksum              51315