Enantioselective Synthesis of Alkylthioetherpyrrolidine Derivatives via [3+2] Cycloaddition of α-Thioacrylates with Isocyanoacetates.
Wang, Zhi-Peng; Li, Zi-Rui; Wu, Qi; Peng, Xiao-Jiao; Shao, Pan-Lin; He, Yun; The Journal of organic chemistry 82 (2017) 12869–12876; doi:10.1021/acs.joc.7b02266

data_4033126
_publ_section_title
;
 Enantioselective Synthesis of Alkylthioetherpyrrolidine Derivatives via
 [3+2] Cycloaddition of \a-Thioacrylates with Isocyanoacetates.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12869
_journal_page_last               12876
_journal_paper_doi               10.1021/acs.joc.7b02266
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H24 N2 O8 S2'
_chemical_formula_sum            'C18 H24 N2 O8 S2'
_chemical_formula_weight         460.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 89.670(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4609(5)
_cell_length_b                   9.5520(4)
_cell_length_c                   12.1087(5)
_cell_measurement_reflns_used    3233
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7770
_cell_measurement_theta_min      3.4490
_cell_volume                     1094.25(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -33.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231   38.0000  150.0000 87

  2 omega   39.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  178.0000    0.0000 25

  3 omega  -25.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -86.0000   -3.0000 28

  4 omega  -21.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -180.0000 42

  5 omega  -70.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -38.0000   30.0000 47

  6 omega  -69.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -19.0000  -60.0000 83

  7 omega  -79.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -57.0000  -90.0000 77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0649067000
_diffrn_orient_matrix_UB_12      0.0372363000
_diffrn_orient_matrix_UB_13      0.0002874000
_diffrn_orient_matrix_UB_21      -0.0322139000
_diffrn_orient_matrix_UB_22      0.0541573000
_diffrn_orient_matrix_UB_23      0.0312707000
_diffrn_orient_matrix_UB_31      0.0195014000
_diffrn_orient_matrix_UB_32      -0.0344874000
_diffrn_orient_matrix_UB_33      0.0495036000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.031
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4473
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0503P)^2^+0.2977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3987
_reflns_number_total             4473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02266_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4033126--4033127.cif.'
_cod_database_code               4033126
_chemical_oxdiff_formula         c18h24n2o8s2
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.893
_reflns_odcompleteness_completeness 99.71
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C),
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              17188
_shelx_hkl_checksum              25874
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'