Scandium Pentafluorobenzoate-Catalyzed Unexpected Cascade Reaction of 2-Aminobenzaldehydes with Primary Amines: A Process for the Preparation of Ring-Fused Aminals
Dan Mao; Jun Tang; Wenbo Wang; Shengying Wu; Xin Liu; Jianjun Yu; Limin Wang; Journal of Organic Chemistry 78 (2013) 12848–12854; doi:10.1021/jo402331t

data_4028886
_publ_section_title
;
 Scandium Pentafluorobenzoate-Catalyzed Unexpected Cascade Reaction of
 2-Aminobenzaldehydes with Primary Amines: A Process for the Preparation
 of Ring-Fused Aminals
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12848
_journal_page_last               12854
_journal_paper_doi               10.1021/jo402331t
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C21 H19 N3'
_chemical_formula_weight         313.39
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5666(6)
_cell_length_b                   20.5185(17)
_cell_length_c                   21.1660(18)
_cell_measurement_reflns_used    4382
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.593
_cell_measurement_theta_min      5.538
_cell_volume                     3286.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16623
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78471
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.255
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.067
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.7052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                2625
_reflns_number_total             3228
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402331t_si_002.cif
_cod_data_source_block           cd211111
_cod_database_code               4028886