Stereoselective synthesis of 3,4-disubstituted and 3,4,5-trisubstituted piperidines by Lewis acid-catalysed ene cyclisation of 4-aza-1,7-dienes.
Walker, Stephen M.; Williams, Jodi T.; Russell, Alexander G.; Kariuki, Benson M.; Snaith, John S.; Organic & biomolecular chemistry 5 (2007) 2925–2931; doi:10.1039/b708139a

data_7151151
_publ_section_title
;
 Stereoselective synthesis of 3,4-disubstituted and
 3,4,5-trisubstituted piperidines by Lewis acid-catalysed ene
 cyclisation of 4-aza-1,7-dienes.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2925
_journal_page_last               2931
_journal_paper_doi               10.1039/b708139a
_journal_volume                  5
_journal_year                    2007
_chemical_formula_moiety         'C20 H26 N2 O5 S, C H CL3'
_chemical_formula_sum            'C21 H27 Cl3 N2 O5 S'
_chemical_formula_weight         525.86
_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                81.993(5)
_cell_angle_beta                 86.709(5)
_cell_angle_gamma                78.059(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0833(5)
_cell_length_b                   9.5865(7)
_cell_length_c                   22.1903(17)
_cell_measurement_reflns_used    2208
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.42
_cell_measurement_theta_min      4.03
_cell_volume                     1253.19(17)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.867
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8035
_diffrn_reflns_theta_full        70.42
_diffrn_reflns_theta_max         70.42
_diffrn_reflns_theta_min         4.03
_exptl_absorpt_coefficient_mu    4.383
_exptl_absorpt_correction_T_max  0.8442
_exptl_absorpt_correction_T_min  0.4744
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                2208
_reflns_number_total             4167
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b708139a.txt
_cod_data_source_block           sw1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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-1
_cod_database_code               7151151