The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids.
Pavlovskaya, Tatyana L.; Yaremenko, Fedor G.; Lipson, Victoria V.; Shishkina, Svetlana V.; Shishkin, Oleg V.; Musatov, Vladimir I.; Karpenko, Alexander S.; Beilstein journal of organic chemistry 10 (2014) 117–126; doi:10.3762/bjoc.10.8

data_4028969
_publ_section_title
;
 The regioselective synthesis of spirooxindolo pyrrolidines and
 pyrrolizidines via three-component reactions of acrylamides and
 aroylacrylic acids with isatins and \a-amino acids.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              117
_journal_page_last               126
_journal_paper_doi               10.3762/bjoc.10.8
_journal_volume                  10
_journal_year                    2014
_chemical_formula_moiety         'C20 H15 Br Cl2 N2 O4, C H4 O'
_chemical_formula_sum            'C21 H19 Br Cl2 N2 O5'
_chemical_formula_weight         530.19
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.858(5)
_cell_angle_beta                 84.297(5)
_cell_angle_gamma                76.237(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8751(7)
_cell_length_b                   10.5764(9)
_cell_length_c                   12.3519(10)
_cell_measurement_reflns_used    9455
_cell_measurement_temperature    466(2)
_cell_measurement_theta_max      32.1
_cell_measurement_theta_min      2.9
_cell_volume                     1090.96(16)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      466(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15210
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    2.165
_exptl_absorpt_correction_T_max  0.6713
_exptl_absorpt_correction_T_min  0.5628
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0528P)^2^+0.1236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                2435
_reflns_number_total             3801
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-8-S4.cif
_cod_data_source_block           experimental
_cod_original_cell_volume        1090.96(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4028969