An organocatalytic domino Michael-alkylation reaction: highly enantioselective construction of spiro-cyclopentanoneoxindoles and tetronic acid scaffolds
Jing Zhou; Qi-Lin Wang; Lin Peng; Fang Tian; Xiao-Ying Xu; Li-Xin Wang; Chem.Commun. 50 (2014) 14601–; doi:10.1039/C4cc05207B

data_7115952
_publ_section_title
;
 An organocatalytic domino Michael-alkylation reaction: highly
 enantioselective construction of spiro-cyclopentanoneoxindoles and
 tetronic acid scaffolds
;
_journal_name_full               Chem.Commun.
_journal_page_first              14601
_journal_paper_doi               10.1039/C4cc05207B
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C54 H52 Br2 N2 O14'
_chemical_formula_weight         1112.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.115(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0921(5)
_cell_length_b                   12.0539(5)
_cell_length_c                   18.6826(8)
_cell_measurement_reflns_used    4355
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      29.0663
_cell_measurement_theta_min      3.0532
_cell_volume                     2680.8(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.903
_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  0.0399
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29024
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.131
_diffrn_reflns_theta_min         3.059
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.004(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         12422
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1458
_refine_ls_R_factor_gt           0.0658
_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^)+(0.0816P)^2^+0.7871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1806
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                6446
_reflns_number_total             12422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc05207b2.cif
_cod_data_source_block           shelxl
_cod_database_code               7115952
_shelx_estimated_absorpt_t_min   0.593
_shelx_estimated_absorpt_t_max   0.649
_shelxl_version_number           2013-4
_shelx_res_checksum              64572
_shelx_hkl_checksum              89775