An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly Functionalized Tetrahydropyridines
Xue-Feng Zhu; Jie Lan; Ohyun Kwon; Journal of the American Chemical Society 125 (2003) 4716–4717; doi:10.1021/ja0344009

data_4113672
_publ_section_title
;
 An Expedient Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Highly
 Functionalized Tetrahydropyridines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4716
_journal_page_last               4717
_journal_paper_doi               10.1021/ja0344009
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C21 H23 N O4 S'
_chemical_formula_weight         385.46
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 116.715(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.961(3)
_cell_length_b                   9.4548(16)
_cell_length_c                   15.518(3)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.85
_cell_measurement_theta_min      2.66
_cell_volume                     1960.8(6)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.818
_diffrn_measured_fraction_theta_max 0.818
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10405
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs(Bruker)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       irregular
_exptl_crystal_F_000             816
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .18
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.837
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.837
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.799
_refine_ls_shift/su_mean         0.056
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                1868
_reflns_number_total             3975
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0344009si20030129_020010.cif
_cod_data_source_block           kw502
_cod_original_cell_volume        1960.7(6)
_cod_database_code               4113672