Highly Diastereoselective Functionalization of Piperidines by Photoredox Catalyzed α-Amino C-H Arylation and Epimerization.
Walker, Morgan M.; Koronkiewicz, Brian; Chen, Shuming; Houk, K. N.; Mayer, James M.; Ellman, Jonathan A.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b13165

data_4134797
_publ_section_title
;
 Highly Diastereoselective Functionalization of Piperidines by Photoredox
 Catalyzed \a-Amino C-H Arylation and Epimerization.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13165
_journal_year                    2020
_chemical_formula_moiety         'C6 H2 N3 O9 S, C16 H26 N, 0.5(C7 H8)'
_chemical_formula_sum            'C25.5 H32 N4 O9 S'
_chemical_formula_weight         570.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.1140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.09190(10)
_cell_length_b                   21.6444(3)
_cell_length_c                   15.4490(2)
_cell_measurement_reflns_used    41131
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.5540
_cell_measurement_theta_min      3.0680
_cell_volume                     2705.80(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1818
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4779
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.639
_diffrn_reflns_theta_max         66.639
_diffrn_reflns_theta_min         3.515
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       Block
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+4.8493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4483
_reflns_number_total             4779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13165_si_004.cif
_cod_data_source_block           007a-20018
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C25.50 H32 N4 O9 S'
_cod_database_code               4134797
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.722
_shelx_estimated_absorpt_t_max   0.786
_shelx_res_checksum              27856
_shelx_hkl_checksum              7348