Enantioselective Diels-Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst.
Kohari, Yoshihito; Okuyama, Yuko; Kwon, Eunsang; Furuyama, Taniyuki; Kobayashi, Nagao; Otuki, Teppei; Kumagai, Jun; Seki, Chigusa; Uwai, Koji; Dai, Gang; Iwasa, Tatsuo; Nakano, Hiroto; The Journal of organic chemistry 79 (2014) 9500–9511; doi:10.1021/jo501433c

data_4030028
_publ_section_title
;
 Enantioselective Diels-Alder Reaction of 1,2-Dihydropyridines with
 Aldehydes Using \b-Amino Alcohol Organocatalyst.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9500
_journal_page_last               9511
_journal_paper_doi               10.1021/jo501433c
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H14 Br N O4'
_chemical_formula_sum            'C15 H14 Br N O4'
_chemical_formula_weight         352.18
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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
_cell_angle_alpha                93.440(18)
_cell_angle_beta                 106.670(16)
_cell_angle_gamma                109.007(16)
_cell_formula_units_Z            1
_cell_length_a                   6.283(11)
_cell_length_b                   7.551(13)
_cell_length_c                   8.088(13)
_cell_measurement_reflns_used    989
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.59
_cell_volume                     342.5(10)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3368
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.025
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             178.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.460
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1250 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.010(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     3
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0043P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                2422
_reflns_number_total             2808
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo501433c_si_002.cif
_cod_data_source_block           05_H
_cod_depositor_comments
'Adding full bibliography for 4030027--4030028.cif.'
_cod_database_code               4030028