Chemo- and Regioselective Asymmetric Synthesis of Cyclic Enamides through the Catalytic Umpolung Organocascade Reaction of α-Imino Amides.
Yoshida, Yasushi; Hiroshige, Tomohiko; Omori, Kazuki; Mino, Takashi; Sakamoto, Masami; The Journal of organic chemistry 84 (2019) 7362–7371; doi:10.1021/acs.joc.9b01036

data_4034627
_publ_section_title
;
 Chemo- and Regioselective Asymmetric Synthesis of Cyclic Enamides through
 the Catalytic Umpolung Organocascade Reaction of \a-Imino Amides.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7362
_journal_page_last               7371
_journal_paper_doi               10.1021/acs.joc.9b01036
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C23 H21 N3 O3'
_chemical_formula_weight         387.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.7396(4)
_cell_length_b                   8.9839(2)
_cell_length_c                   21.9017(5)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.2242
_cell_measurement_theta_min      4.0370
_cell_volume                     4080.78(15)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31753
_diffrn_reflns_theta_full        68.285
_diffrn_reflns_theta_max         68.285
_diffrn_reflns_theta_min         4.037
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+1.0087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                3314
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01036_si_002.cif
_cod_data_source_block           I
_cod_database_code               4034627
_shelx_res_checksum              40442
_shelx_hkl_checksum              19013