Selective Synthesis of N-Substituted 1,2-Dihydropyridines from Furans by Copper-Induced Concurrent Tandem Catalysis
Manuel R. Fructos; Eleuterio Álvarez; M. Mar Díaz-Requejo; Pedro J. Pérez; Journal of the American Chemical Society 132 (2010) 4600–4607; doi:10.1021/ja1006614

data_4102217
_publ_section_title
;
 Selective Synthesis of N-Substituted 1,2-Dihydropyridines from Furans by
 Copper-Induced Concurrent Tandem Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4600
_journal_page_last               4607
_journal_paper_doi               10.1021/ja1006614
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C19 H23 N O4 S'
_chemical_formula_sum            'C19 H23 N O4 S'
_chemical_formula_weight         361.44
_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                95.288(3)
_cell_angle_beta                 96.482(3)
_cell_angle_gamma                102.289(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8803(8)
_cell_length_b                   9.2429(8)
_cell_length_c                   11.5508(11)
_cell_measurement_reflns_used    9004
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.97
_cell_measurement_theta_min      2.70
_cell_volume                     913.82(14)
_computing_cell_refinement       'Bruker (2006). APEX 2. Version 2.1.'
_computing_data_collection       'Bruker (2006). APEX 2. Version 2.1.'
_computing_data_reduction        'Bruker (2006). APEX 2. Version 2.1.'
_computing_molecular_graphics    'XP, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_publication_material  'XCIF, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_structure_refinement  'XL, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_structure_solution    'Bruker (2006). APEX 2. Version 2.1.'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type
;
 Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            42420
_diffrn_reflns_theta_full        30.67
_diffrn_reflns_theta_max         30.67
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.9278
_exptl_absorpt_correction_T_min  0.9066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical
 X-ray Solutions, Madison, Wisconsin, USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         5549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0506P)^2^+0.3773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                5210
_reflns_number_total             5549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1006614_si_001.cif
_cod_data_source_block           COMPOUND_2
_cod_database_code               4102217