Stereoselective Synthesis of 2,4,5-Trisubstituted Piperidines via Radical Cyclization
Maria-Eleni Ragoussi; Stephen M. Walker; Andrea Piccanello; Benson M. Kariuki; Peter N. Horton; Neil Spencer; John S. Snaith; Journal of Organic Chemistry 75 (2010) 7347–7357; doi:10.1021/jo101631y

data_4025774
_publ_contact_author
;
B. Kariuki,
School of Chemistry,
Cardiff University,
Main Building
Park Place
Cardiff
CF10 3AT
;
_publ_section_title
;
 Stereoselective Synthesis of 2,4,5-Trisubstituted Piperidines via Radical
 Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7347
_journal_page_last               7357
_journal_paper_doi               10.1021/jo101631y
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H29 N O4 S'
_chemical_formula_weight         463.57
_space_group_IT_number           1
_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                100.376(2)
_cell_angle_beta                 91.9860(10)
_cell_angle_gamma                99.810(2)
_cell_formula_units_Z            4
_cell_length_a                   11.2986(3)
_cell_length_b                   14.5663(4)
_cell_length_c                   15.2241(4)
_cell_measurement_reflns_used    10962
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     2423.03(11)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            51830
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Slab
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       0.0062(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1214
_refine_ls_number_reflns         20930
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0457P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                14534
_reflns_number_total             20930
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101631y_si_001.cif
_cod_data_source_block           2008src0632
_cod_database_code               4025774