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_4033127
_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 ad
_chemical_formula_sum            'C21 H15 Cl N2 O6'
_chemical_formula_weight         426.80
_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                   7.2342(2)
_cell_length_b                   7.6993(2)
_cell_length_c                   34.2572(7)
_cell_measurement_reflns_used    7253
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.9100
_cell_measurement_theta_min      3.5420
_cell_volume                     1908.07(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            21376
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.086
_diffrn_reflns_theta_min         3.334
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95151
_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_colour            Colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1236 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0279P)^2^+0.7474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                3771
_reflns_number_total             4618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02266_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4033126--4033127.cif.'
_cod_database_code               4033127
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              60222
_shelx_hkl_checksum              61875