Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and Spirooxindoles via Allylic Alkylation of Morita-Baylis-Hillman Carbonates of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO.
Arupula, Sanjeeva K.; Guin, Soumitra; Yadav, Anubha; Mobin, Shaikh M.; Samanta, Sampak; The Journal of organic chemistry 83 (2018) 2660–2675; doi:10.1021/acs.joc.7b03090

data_4034965
_publ_section_title
;
 Stereoselective Synthesis of 3,3-Disubstituted Oxindoles and
 Spirooxindoles via Allylic Alkylation of Morita-Baylis-Hillman Carbonates
 of Isatins with Cyclic Sulfamidate Imines Catalyzed by DABCO.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2660
_journal_page_last               2675
_journal_paper_doi               10.1021/acs.joc.7b03090
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C56 H48 N4 O12 S2'
_chemical_formula_weight         1033.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                87.500(9)
_cell_angle_beta                 89.642(9)
_cell_angle_gamma                81.926(6)
_cell_formula_units_Z            2
_cell_length_a                   9.1196(7)
_cell_length_b                   10.5626(7)
_cell_length_c                   25.628(4)
_cell_measurement_reflns_used    2178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5120
_cell_measurement_theta_min      3.6160
_cell_volume                     2441.9(5)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       \w/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23094
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.276
_diffrn_reflns_theta_min         3.016
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56416
_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            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         11124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0576P)^2^+0.8622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8373
_reflns_number_total             11124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03090_si_004.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2441.8(4)
_cod_database_code               4034965
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              41474
_shelx_hkl_checksum              27913