Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones
Trung Cao; Elizabeth C. Linton; Joshua Deitch; Simon Berritt; Marisa C. Kozlowski; Journal of Organic Chemistry 77 (2012) 11034–11055; doi:10.1021/jo302039n

data_4027779
_publ_section_title
;
 Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen
 Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary
 Oxindoles and Spirocyclic Lactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11034
_journal_page_last               11055
_journal_paper_doi               10.1021/jo302039n
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H31 N O3 Si'
_chemical_formula_weight         385.57
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6875(13)
_cell_length_b                   14.688(2)
_cell_length_c                   16.685(2)
_cell_measurement_temperature    143(1)
_cell_volume                     2129.0(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18547
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
   Shape function based on spherical harmonics.
   Highest even and odd order for spherical harmonics:  4  and  3
   Laue group:  mmm
;
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), 1607 Friedel pairs'
_refine_ls_abs_structure_Flack   0.11(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0356P)^2^+0.5537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                3126
_reflns_number_total             3772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302039n_si_002_1.cif
_cod_data_source_block           CMPD8s
_cod_original_cell_volume        2129.1(5)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4027779