Organocatalytic asymmetric multicomponent reactions of aromatic aldehydes and anilines with β-ketoesters: facile and atom-economical access to chiral tetrahydropyridines
Li, Xuejian; Zhao, Yanyan; Qu, Haijun; Mao, Zhenjun; Lin, Xufeng; Chemical Communications (Cambridge, United Kingdom) 49 (2013) 1401–1403; doi:10.1039/c2cc38349g

data_7112436
_publ_section_title
;
 Organocatalytic asymmetric multicomponent reactions of aromatic aldehydes
 and anilines with \b-ketoesters: facile and atom-economical access to
 chiral tetrahydropyridines
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   14
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1401
_journal_page_last               1403
_journal_paper_doi               10.1039/c2cc38349g
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H32 N4 O6'
_chemical_formula_sum            'C34 H32 N4 O6'
_chemical_formula_weight         592.64
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 113.134(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.5684(2)
_cell_length_b                   10.37340(15)
_cell_length_c                   13.8042(3)
_cell_measurement_reflns_used    7742
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3700
_cell_measurement_theta_min      3.4788
_cell_volume                     1523.35(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13194
_diffrn_reflns_theta_full        67.48
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.8670
_exptl_absorpt_correction_T_min  0.8320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack (1983), 2523 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0062(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5419
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.1808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                4992
_reflns_number_total             5419
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7108840
_cod_data_source_file            c2cc38349g.txt
_cod_data_source_block           120601_lxj_24
_cod_original_cell_volume        1523.34(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7112436