An asymmetric alkynylation/hydrothiolation cascade: an enantioselective synthesis of thiazolidine-2-imines from imines, acetylenes and isothiocyanates
Alok Ranjan; Anupam Mandal; Swapnil G. Yerande; Dattatraya H. Dethe; Chem.Commun. 51 (2015) 14215–; doi:10.1039/C5cc05549K

data_7117758
_publ_section_title
;
 An asymmetric alkynylation/hydrothiolation cascade: an enantioselective
 synthesis of thiazolidine-2-imines from imines, acetylenes and
 isothiocyanates
;
_journal_name_full               Chem.Commun.
_journal_page_first              14215
_journal_paper_doi               10.1039/C5cc05549K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C30 H26 N2 S'
_chemical_formula_weight         446.59
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-29 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.669(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.059(5)
_cell_length_b                   5.6470(14)
_cell_length_c                   42.733(11)
_cell_measurement_temperature    100(2)
_cell_volume                     4590(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            11767
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         0.95
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1085P)^2^+3.6368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1794
_reflns_number_gt                3420
_reflns_number_total             4252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05549k2.cif
_cod_data_source_block           10nova
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7117758