Synthesis of spirocarbamate oxindoles via intramolecular trapping of a β-silyl carbocation by an N-Boc group.
Shupe, Benjamin H.; Allen, Emily E.; MacDonald, Jacob P.; Wilson, Sean O.; Franz, Annaliese K.; Organic letters 15 (2013) 3218–3221; doi:10.1021/ol4010867

data_1556160
_publ_section_title
;
 Synthesis of spirocarbamate oxindoles via intramolecular trapping of a
 \b-silyl carbocation by an N-Boc group.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3218
_journal_page_last               3221
_journal_paper_doi               10.1021/ol4010867
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C22 H33 F N2 O3 Si, C H2 Cl2'
_chemical_formula_sum            'C23 H35 Cl2 F N2 O3 Si'
_chemical_formula_weight         505.52
_chemical_name_common            'oxindole with methylene chloride solvate'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.2630(10)
_cell_angle_beta                 76.6630(10)
_cell_angle_gamma                84.8420(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2544(6)
_cell_length_b                   10.1036(7)
_cell_length_c                   14.0370(10)
_cell_measurement_reflns_used    2099
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      3.1
_cell_volume                     1271.89(15)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12368
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.9367
_exptl_absorpt_correction_T_min  0.8142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.492
_refine_diff_density_min         -1.100
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         5637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.091
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+1.1801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                5072
_reflns_number_total             5637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4010867_si_001.cif
_cod_data_source_block           sw1
_cod_database_code               1556160