Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with α,β-Unsaturated Acyl Phosphonates for the Construction of Spirocyclic Oxindole-γ-lactones/lactams.
Chen, Lin; Wu, Zhi-Jun; Zhang, Ming-Liang; Yue, Deng-Feng; Zhang, Xiao-Mei; Xu, Xiao-Ying; Yuan, Wei-Cheng; The Journal of organic chemistry 80 (2015) 12668–12675; doi:10.1021/acs.joc.5b02253

data_4036499
_publ_section_title
;
 Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of
 3-Hydroxyoxindoles/3-Aminooxindoles with \a,\b-Unsaturated Acyl
 Phosphonates for the Construction of Spirocyclic
 Oxindole-\g-lactones/lactams.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12668
_journal_page_last               12675
_journal_paper_doi               10.1021/acs.joc.5b02253
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H12 Br N O3'
_chemical_formula_weight         310.15
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5256(7)
_cell_length_b                   9.8263(10)
_cell_length_c                   14.0527(11)
_cell_measurement_reflns_used    2001
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      21.6140
_cell_measurement_theta_min      4.1410
_cell_volume                     1315.35(19)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11571
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.205
_diffrn_reflns_theta_min         3.565
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48538
_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    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.390
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.178
_refine_ls_abs_structure_details
;
 Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.004(11)
_refine_ls_extinction_coef       0.037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0771P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                1986
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02253_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4036499
_shelx_estimated_absorpt_t_min   0.354
_shelx_estimated_absorpt_t_max   0.375
_shelxl_version_number           2013-4
_shelx_res_checksum              57338
_shelx_hkl_checksum              53416