Me~3~SiCl-Promoted Three-Component Coupling Reaction of a Functionalized Enamine, an Acetal, and an Alkyne: An Unprecedented Approach to the Synthesis of Tetrasubstituted Pyridines via a [3 + 2 + 1] Intermolecular Cyclization
Toshiaki Sasada; Norio Sakai; Takeo Konakahara; Journal of Organic Chemistry 73 (2008) 6905–6908; doi:10.1021/jo801090h

data_4023647
_publ_section_title
;
 Me~3~SiCl-Promoted Three-Component Coupling Reaction of a
 Functionalized Enamine, an Acetal, and an Alkyne: An Unprecedented
 Approach to the Synthesis of Tetrasubstituted Pyridines via
 a [3 + 2 + 1] Intermolecular Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6905
_journal_page_last               6908
_journal_paper_doi               10.1021/jo801090h
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C20 H18 N2 O6'
_chemical_formula_weight         382.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.596(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7232(10)
_cell_length_b                   24.783(4)
_cell_length_c                   10.9025(16)
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    273
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.49
_cell_volume                     1808.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      273
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10719
_diffrn_reflns_theta_full        28.21
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.1298
_refine_ls_shift/su_max          0.092
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0976P)^2^+17.9884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3149
_refine_ls_wR_factor_ref         0.3179
_reflns_number_gt                3840
_reflns_number_total             4068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801090h-file002.cif
_cod_data_source_block           t40s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023647