Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications
Catherine Gomez; Maxime Gicquel; Jean-Christophe Carry; Laurent Schio; Pascal Retailleau; Arnaud Voituriez; Angela Marinetti; Journal of Organic Chemistry 78 (2013) 1488–1496; doi:10.1021/jo302460d

data_4027959
_publ_contact_author_address
;Centre de Recherche de Gif
Institut de Chimie des Substances Naturelles
UPR2301-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email       angela.marinetti@icsn.cnrs-gif.fr
_publ_contact_author_fax         +33169077247
_publ_contact_author_name
;
'MARINETTI, Angela'
;
_publ_contact_author_phone       +33169823036
_publ_section_title
;
 Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from
 \g-Substituted Allenoates: Systematic Studies and Targeted Applications
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1488
_journal_page_last               1496
_journal_paper_doi               10.1021/jo302460d
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C28 H28 Cl2 F N O4'
_chemical_formula_sum            'C28 H28 Cl2 F N O4'
_chemical_formula_weight         532.41
_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                81.087(3)
_cell_angle_beta                 72.553(5)
_cell_angle_gamma                74.450(4)
_cell_formula_units_Z            2
_cell_length_a                   10.868(2)
_cell_length_b                   10.960(3)
_cell_length_c                   12.176(3)
_cell_measurement_reflns_used    3482
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.817
_cell_measurement_theta_min      0.407
_cell_volume                     1328.6(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9674
_diffrn_reflns_theta_full        23.80
_diffrn_reflns_theta_max         23.80
_diffrn_reflns_theta_min         1.76
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       platelet
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.030(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   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+1.0309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1710
_refine_ls_wR_factor_ref         0.1960
_reflns_number_gt                2758
_reflns_number_total             4005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302460d_si_002_5.cif
_cod_data_source_block           compound_10-B_ccdc_890166
_cod_database_code               4027959