Asymmetric Synthesis of γ-Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts.
Peraino, Nicholas J.; Kaster, Sven H.; Wheeler, Kraig A.; Kerrigan, Nessan J.; The Journal of organic chemistry 82 (2017) 606–615; doi:10.1021/acs.joc.6b02622

data_4032094
_publ_section_title
;
 Asymmetric Synthesis of \g-Lactones through Koga Amine-Controlled
 Addition of Enediolates to \a,\b-Unsaturated Sulfoxonium Salts.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              606
_journal_page_last               615
_journal_paper_doi               10.1021/acs.joc.6b02622
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3581(6)
_cell_length_b                   11.1996(8)
_cell_length_c                   15.9048(10)
_cell_measurement_reflns_used    8191
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.02
_cell_measurement_theta_min      4.83
_cell_volume                     1488.81(18)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22316
_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         68.190
_diffrn_reflns_theta_min         4.829
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       'transparent plate'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0378P)^2^+0.1287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0690
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2602
_reflns_number_total             2727
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02622_si_002.cif
_cod_data_source_block           nker18a
_cod_depositor_comments          'Adding full bibliography for 4032094.cif.'
_cod_database_code               4032094
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.815
_shelx_estimated_absorpt_t_max   0.958
_shelx_res_checksum              23305
_shelx_hkl_checksum              95885