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_4134799
_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         'C23 H29 N2, C6 H2 N3 O9 S'
_chemical_formula_sum            'C29 H31 N5 O9 S'
_chemical_formula_weight         625.65
_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   geom
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.656(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1117(3)
_cell_length_b                   19.7564(8)
_cell_length_c                   18.3015(9)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      58.5180
_cell_measurement_theta_min      3.2430
_cell_volume                     2929.8(2)
_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 1.000
_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  0.2324
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5182
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.294
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5182
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0910
_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^)+(0.0939P)^2^+4.9072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             5182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13165_si_005.cif
_cod_data_source_block           007b-20020
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4134799
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              8034
_shelx_hkl_checksum              1428