Diastereoselective synthesis of γ-lactones through reaction of enediolates with α,β-unsaturated sulfoxonium salts.
Peraino, Nicholas J.; Wheeler, Kraig A.; Kerrigan, Nessan J.; Organic letters 17 (2015) 1735–1737; doi:10.1021/acs.orglett.5b00545

data_1554873
_publ_section_title
;
 Diastereoselective synthesis of \g-lactones through reaction of
 enediolates with \a,\b-unsaturated sulfoxonium salts.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1735
_journal_page_last               1737
_journal_paper_doi               10.1021/acs.orglett.5b00545
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H16 O2'
_chemical_formula_sum            'C20 H16 O2'
_chemical_formula_weight         288.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9724(4)
_cell_length_b                   14.8969(10)
_cell_length_c                   16.4863(11)
_cell_measurement_reflns_used    4519
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.330
_cell_measurement_theta_min      3.856
_cell_volume                     1466.79(17)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21860
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.999
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       'transparent needle'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.1366P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.001
_reflns_number_gt                2415
_reflns_number_total             2688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00545_si_003.cif
_cod_data_source_block           nker10
_cod_database_code               1554873
_shelx_estimated_absorpt_t_min   0.747
_shelx_estimated_absorpt_t_max   0.923
_shelxl_version_number           2012-9
_shelx_res_checksum              97979
_shelx_hkl_checksum              47766