Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated Piperidines from Tetrahydropyridines.
Chen, Shuming; Mercado, Brandon Q.; Bergman, Robert G.; Ellman, Jonathan A.; The Journal of organic chemistry 80 (2015) 6660–6668; doi:10.1021/acs.joc.5b00816

data_4031143
_publ_section_title
;
 Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated
 Piperidines from Tetrahydropyridines.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6660
_journal_page_last               6668
_journal_paper_doi               10.1021/acs.joc.5b00816
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C25 H32 N4 O10 S'
_chemical_formula_weight         580.61
_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                 92.979(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2479(2)
_cell_length_b                   12.9727(2)
_cell_length_c                   20.7998(15)
_cell_measurement_reflns_used    40942
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      2.1
_cell_volume                     2761.4(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            42603
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         4.26
_exptl_absorpt_coefficient_mu    1.589
_exptl_absorpt_correction_T_max  0.6921
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4914
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0516P)^2^+1.2296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                4827
_reflns_number_total             4914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            4a_1000666.cif
_cod_data_source_block           12109
_cod_depositor_comments
'Adding full bibliography for 4031139--4031144.cif.'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4031143