Asymmetric synthesis of trisubstituted tetrahydrothiophenes bearing a quaternary stereocenter via double Michael reaction involving dynamic kinetic resolution.
Meninno, Sara; Croce, Gianluca; Lattanzi, Alessandra; Organic letters 15 (2013) 3436–3439; doi:10.1021/ol4014975

data_1556211
_publ_section_title
;
 Asymmetric synthesis of trisubstituted tetrahydrothiophenes bearing a
 quaternary stereocenter via double Michael reaction involving dynamic
 kinetic resolution.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3436
_journal_page_last               3439
_journal_paper_doi               10.1021/ol4014975
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H24 N2 O5 S'
_chemical_formula_sum            'C24 H24 N2 O5 S'
_chemical_formula_weight         452.51
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-12-18 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.667(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1070(6)
_cell_length_b                   6.8488(5)
_cell_length_c                   16.9251(12)
_cell_measurement_reflns_used    15078
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2988
_cell_measurement_theta_min      4.1115
_cell_volume                     1171.49(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.962
_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  0.0999
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            48340
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                3233
_reflns_number_total             5483
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4014975_si_001.cif
_cod_data_source_block           start
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1556211
_cell_oxdiff_length_a            10.1033(4)
_cell_oxdiff_length_b            6.8432(3)
_cell_oxdiff_length_c            16.9077(7)
_cell_oxdiff_angle_alpha         89.993(3)
_cell_oxdiff_angle_beta          90.682(3)
_cell_oxdiff_angle_gamma         89.985(4)
_cell_oxdiff_volume              1168.90(9)
_cell_oxdiff_measurement_reflns_used 15078