Lewis Acid-Catalyzed Cyclization of Enaminones with Propargylic Alcohols: Regioselective Synthesis of Multisubstituted 1,2-Dihydropyridines
Yushang Shao; Kai Zhu; Zhengchen Qin; Ende Li; Yanzhong Li; Journal of Organic Chemistry 78 (2013) 5731–5736; doi:10.1021/jo4005553

data_4028285
_publ_section_title
;
 Lewis Acid-Catalyzed Cyclization of Enaminones with Propargylic Alcohols:
 Regioselective Synthesis of Multisubstituted 1,2-Dihydropyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5731
_journal_page_last               5736
_journal_paper_doi               10.1021/jo4005553
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H28 N2 O3'
_chemical_formula_weight         500.57
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            16
_cell_length_a                   18.050(2)
_cell_length_b                   35.092(4)
_cell_length_c                   16.8645(19)
_cell_measurement_reflns_used    2442
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.101
_cell_measurement_theta_min      4.801
_cell_volume                     10682(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15681
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09466
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             4224
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.9(19)
_refine_ls_extinction_coef       0.00019(6)
_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   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                2830
_reflns_number_total             5126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4005553_si_003.cif
_cod_data_source_block           cd212316
_cod_database_code               4028285