Indium-Catalyzed Amide Allylation of N-Carbonyl Imides: Formation of Azaspiro-γ-lactones via Ring Opening-Reclosure.
Sengoku, Tetsuya; Murata, Yusuke; Aso, Yuwa; Kawakami, Ai; Inuzuka, Toshiyasu; Sakamoto, Masami; Takahashi, Masaki; Yoda, Hidemi; Organic letters 17 (2015) 5846–5849; doi:10.1021/acs.orglett.5b03021

data_1555441
_publ_section_title
;
 Indium-Catalyzed Amide Allylation of N-Carbonyl Imides: Formation of
 Azaspiro-\g-lactones via Ring Opening-Reclosure.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5846
_journal_page_last               5849
_journal_paper_doi               10.1021/acs.orglett.5b03021
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C18 H13 N O3'
_chemical_formula_weight         291.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.246(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2686(15)
_cell_length_b                   16.156(3)
_cell_length_c                   9.4109(16)
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.4165
_cell_measurement_theta_min      2.5125
_cell_volume                     1403.3(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  goniometer
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7859
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0474P)^2^+0.3559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                2779
_reflns_number_total             3171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03021_si_002.cif
_cod_data_source_block           I
_cod_database_code               1555441