Cinchona Alkaloid Thiourea Mediated Asymmetric Mannich Reaction of Isocyanoacetates with Isatin-Derived Ketimines and Subsequent Cyclization: Enantioselective Synthesis of Spirooxindole Imidazolines
Zhao, Mei-Xin; Jing, Lei; Zhou, Hao; Shi, Min; RSC Adv.  (2015) –; doi:10.1039/C5RA17075C

data_7221981
_publ_section_title
;
 Cinchona Alkaloid Thiourea Mediated Asymmetric Mannich Reaction of
 Isocyanoacetates with Isatin-Derived Ketimines and Subsequent
 Cyclization: Enantioselective Synthesis of Spirooxindole Imidazolines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA17075C
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H26 Br Cl2 N3 O5'
_chemical_formula_weight         599.30
_chemical_name_systematic
'(R)-Methyl 2-((R)-5-bromo-3-((tert-butoxycarbonyl)amino)-1-methyl-2-oxoindolin-3-yl)-2- isocyano-2-phenylacetate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-04 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5000(10)
_cell_length_b                   14.8773(16)
_cell_length_c                   19.875(2)
_cell_measurement_temperature    296(2)
_cell_volume                     2809.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32871
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_T_max  0.6674
_exptl_absorpt_correction_T_min  0.4973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: mixture of dichloromethane and petroleum ether'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.843
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1196P)^2^+1.4879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1774
_reflns_number_gt                4137
_reflns_number_total             4948
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra17075c2.cif
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7221981