Synthesis of polyhydroxylated piperidine and pyrrolidine peptidomimetics via one-pot sequential lactam reduction/Joullié-Ugi reaction.
Szcześniak, Piotr; Maziarz, Elżbieta; Stecko, Sebastian; Furman, Bartłomiej; The Journal of organic chemistry 80 (2015) 3621–3633; doi:10.1021/acs.joc.5b00335

data_4036170
_publ_section_title
;
 Synthesis of polyhydroxylated piperidine and pyrrolidine peptidomimetics
 via one-pot sequential lactam reduction/Joulli\'e-Ugi reaction.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3621
_journal_page_last               3633
_journal_paper_doi               10.1021/acs.joc.5b00335
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C28 H27 F3 N2 O5'
_chemical_formula_sum            'C28 H28 F3 N2 O5'
_chemical_formula_weight         529.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 105.392(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4099(18)
_cell_length_b                   4.9012(7)
_cell_length_c                   21.768(3)
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      2.11
_cell_volume                     1276.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15737
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.578
_diffrn_reflns_theta_min         2.105
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_T_max  0.9310
_exptl_absorpt_correction_T_min  0.7880
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       needle
_exptl_crystal_F_000             554
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details
;
 Flack x determined using 1348 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4176
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0997P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                3666
_reflns_number_total             4176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00335_si_004.cif
_cod_data_source_block           EMR827F3_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036170
_shelx_estimated_absorpt_t_min   0.788
_shelx_estimated_absorpt_t_max   0.931
_shelxl_version_number           2014-3
_shelx_res_checksum              17359
_shelx_hkl_checksum              69659