Indium-catalysed amide allylation of α-iminoamide: highly enantioselective synthesis of amide functionalised α-methylene-γ-butyrolactams.
Sengoku, Tetsuya; Kokubo, Kana; Sakamoto, Masami; Takahashi, Masaki; Yoda, Hidemi; Organic & biomolecular chemistry 15 (2017) 320–323; doi:10.1039/c6ob02506d

data_7155389
_publ_section_title
;
 Indium-catalysed amide allylation of \a-iminoamide: highly
 enantioselective synthesis of amide functionalised
 \a-methylene-\g-butyrolactams.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              320
_journal_page_last               323
_journal_paper_doi               10.1039/c6ob02506d
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H20 Cl N O4'
_chemical_formula_weight         433.87
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_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_update_record
;
2016-11-14 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                82.5366(18)
_cell_angle_beta                 73.6985(14)
_cell_angle_gamma                76.9181(18)
_cell_formula_units_Z            1
_cell_length_a                   6.5505(3)
_cell_length_b                   8.7111(4)
_cell_length_c                   9.9103(5)
_cell_measurement_reflns_used    5852
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.1555
_cell_measurement_theta_min      4.6606
_cell_volume                     527.35(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-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'BRUKER APEX-II CCD'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5780
_diffrn_reflns_theta_full        68.13
_diffrn_reflns_theta_max         68.13
_diffrn_reflns_theta_min         4.66
_exptl_absorpt_coefficient_mu    1.875
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             226
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.263
_refine_ls_abs_structure_details
;
Flack x determined using 711 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.107(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0453P)^2^+0.0976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                2571
_reflns_number_total             2591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02506d2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 7155389.cif.'
_cod_database_code               7155389
_shelx_res_checksum              68852