Catalytic intermolecular hetero-dehydro-Diels-Alder cycloadditions: regio- and diasteroselective synthesis of 5,6-dihydropyridin-2-ones.
Fernández-García, Jesús Manuel; Fernández-Rodríguez, Manuel Á; Aguilar, Enrique; Organic letters 13 (2011) 5172–5175; doi:10.1021/ol202046y

data_1502467
_publ_section_title
;
 Catalytic intermolecular hetero-dehydro-Diels-Alder cycloadditions:
 regio- and diasteroselective synthesis of 5,6-dihydropyridin-2-ones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5172
_journal_page_last               5175
_journal_paper_doi               10.1021/ol202046y
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C27 H22 N2 O5'
_chemical_formula_sum            'C27 H22 N2 O5'
_chemical_formula_weight         454.48
_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                81.355(5)
_cell_angle_beta                 89.502(4)
_cell_angle_gamma                79.460(5)
_cell_formula_units_Z            4
_cell_length_a                   9.8640(5)
_cell_length_b                   13.4240(9)
_cell_length_c                   18.0592(9)
_cell_measurement_reflns_used    3577
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8853
_cell_measurement_theta_min      3.3822
_cell_volume                     2323.8(2)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22699
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.774
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     789
_refine_ls_number_reflns         8907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.774
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0451P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                3249
_reflns_number_total             8907
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol202046y_si_002.cif
_cod_data_source_block           jfg77
_cod_database_code               1502467