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_4028885
_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            'C27 H21 Cl N4'
_chemical_formula_weight         436.93
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                105.802(3)
_cell_angle_beta                 90.987(3)
_cell_angle_gamma                101.867(3)
_cell_formula_units_Z            4
_cell_length_a                   9.4491(16)
_cell_length_b                   12.552(2)
_cell_length_c                   20.936(4)
_cell_measurement_reflns_used    7278
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.49
_cell_volume                     2331.1(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14538
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.9674
_exptl_absorpt_correction_T_min  0.9296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_platon_squeeze_details
;
;
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         8222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1473P)^2^+0.3463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2094
_reflns_number_gt                6531
_reflns_number_total             8222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402331t_si_001.cif
_cod_data_source_block           mo_dm11359_0m
_cod_database_code               4028885