A highly enantioselective Mannich reaction of aldehydes with cyclic N-acyliminium ions by synergistic catalysis
Francesco Berti; Federico Malossi; Fabio Marchetti; Mauro Pineschi; Chem.Commun. 51 (2015) 13694–; doi:10.1039/C5cc04416B

data_7117670
_publ_section_title
;
 A highly enantioselective Mannich reaction of aldehydes with cyclic
 N-acyliminium ions by synergistic catalysis
;
_journal_name_full               Chem.Commun.
_journal_page_first              13694
_journal_paper_doi               10.1039/C5cc04416B
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 Br N O3'
_chemical_formula_sum            'C20 H20 Br N O3'
_chemical_formula_weight         402.28
_chemical_name_systematic
'6-Bromo-2-(hydroxy-phenyl-methyl)-2H-quinoline-1-carboxylic acid ethyl ester'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-03-30T17:21:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-03-30 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.117(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3126(8)
_cell_length_b                   9.6321(13)
_cell_length_c                   18.149(3)
_cell_measurement_reflns_used    5830
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.38
_cell_measurement_theta_min      2.69
_cell_volume                     928.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.048
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17344
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.828
_diffrn_reflns_theta_min         3.838
_exptl_absorpt_coefficient_mu    2.233
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.44
_exptl_crystal_description       'Fragment like arrow pin'
_exptl_crystal_F_000             412
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.019(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4346
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0234P)^2^+0.2178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3585
_reflns_number_total             4346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04416b5.cif
_cod_data_source_block           brochin_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7117670
_shelx_estimated_absorpt_t_min   0.643
_shelx_estimated_absorpt_t_max   0.828