Enantioselective Construction of Spirocyclic Oxindoles via Tandem Michael/Michael Reactions Catalyzed by Multifunctional Quaternary Phosphonium Salt.
Zhang, Jiaxing; Cao, Dongdong; Wang, Hongyu; Zheng, Changwu; Zhao, Gang; Shang, Yongjia; The Journal of organic chemistry 81 (2016) 10558–10568; doi:10.1021/acs.joc.6b01553

data_4037116
_publ_section_title
;
 Enantioselective Construction of Spirocyclic Oxindoles via Tandem
 Michael/Michael Reactions Catalyzed by Multifunctional Quaternary
 Phosphonium Salt.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10558
_journal_page_last               10568
_journal_paper_doi               10.1021/acs.joc.6b01553
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C41 H38 F N O9'
_chemical_formula_sum            'C41 H38 F N O9'
_chemical_formula_weight         707.72
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 108.0760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.4027(5)
_cell_length_b                   8.6895(3)
_cell_length_c                   14.5915(5)
_cell_measurement_reflns_used    9179
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.42
_cell_measurement_theta_min      6.01
_cell_volume                     1736.03(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24202
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.415
_diffrn_reflns_theta_min         3.767
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             674
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         6293
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0410P)^2^+0.1951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0721
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6095
_reflns_number_total             6293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01553_si_001.cif
_cod_data_source_block           p
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037116
_shelxl_version_number           2014-3
_shelx_res_checksum              9546
_shelx_hkl_checksum              42850