Diastereoselective Synthesis of Biheterocyclic Tetrahydrothiophene Derivatives via Base-Catalyzed Cascade Michael-Aldol [3 + 2] Annulation of 1,4-Dithiane-2,5-diol with Maleimides.
Zhong, Yuan; Ma, Shixiong; Li, Bai; Jiang, Xianxing; Wang, Rui; The Journal of organic chemistry 80 (2015) 6870–6874; doi:10.1021/acs.joc.5b00897

data_4031102
_publ_section_title
;
 Diastereoselective Synthesis of Biheterocyclic Tetrahydrothiophene
 Derivatives via Base-Catalyzed Cascade Michael-Aldol [3 + 2] Annulation
 of 1,4-Dithiane-2,5-diol with Maleimides.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6870
_journal_page_last               6874
_journal_paper_doi               10.1021/acs.joc.5b00897
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C18 H15 N O3 S'
_chemical_formula_sum            'C18 H15 N O3 S'
_chemical_formula_weight         325.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-03
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Olex2 1.2
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      291.89(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega   -2.00   25.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000  -48.0000 18

  2 omega   -1.00   38.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000  -60.0000 26

  3 omega    5.00   87.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000  -30.0000 55

  4 omega   -5.00   67.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000 -120.0000 48
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_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
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_diffrn_orient_matrix_UB_21      0.0555748000
_diffrn_orient_matrix_UB_22      0.0175673000
_diffrn_orient_matrix_UB_23      0.0026769000
_diffrn_orient_matrix_UB_31      -0.0099865000
_diffrn_orient_matrix_UB_32      0.1107770000
_diffrn_orient_matrix_UB_33      -0.0120497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0986
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_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5487
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.49
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.226
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
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_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
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'calc w=1/[\s^2^(Fo^2^)+(0.1678P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                1620
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_cod_depositor_comments
'Adding full bibliography for 4031102--4031104.cif.'
_cod_database_code               4031102
_reflns_odcompleteness_completeness 97.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C21(H21), C23(H23), C25(H25), C58(H58), C62(H62),
 C64(H64), C69(H69)
2.d Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_olex2_date_sample_data_collection 1417577938.33
_olex2_submission_special_instructions 'No special instructions were received'