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_4027957
_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         'C26 H28 Cl2 F N O3'
_chemical_formula_sum            'C26 H28 Cl2 F N O3'
_chemical_formula_weight         492.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.468(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.107(3)
_cell_length_b                   23.9229(4)
_cell_length_c                   20.0388(14)
_cell_measurement_reflns_used    11660
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      6.9
_cell_volume                     5131.7(15)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_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      193(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23312
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         6.92
_exptl_absorpt_coefficient_mu    2.560
_exptl_absorpt_correction_T_max  0.488
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         9194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0654P)^2^+1.3610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                7123
_reflns_number_total             9199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302460d_si_002_3.cif
_cod_data_source_block           compound_10A_ccdc_890164
_cod_original_cell_volume        5131.7(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027957