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_4036171
_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_absolute_configuration ad
_chemical_formula_moiety         'C27 H31 F3 N2 O4'
_chemical_formula_sum            'C27 H31 F3 N2 O4'
_chemical_formula_weight         504.54
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 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                 98.831(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.7783(2)
_cell_length_b                   24.114(1)
_cell_length_c                   10.8711(5)
_cell_measurement_reflns_used    5977
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      72.015
_cell_measurement_theta_min      3.663
_cell_volume                     1237.76(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 16.297
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8876
_diffrn_reflns_theta_full        72.16
_diffrn_reflns_theta_max         72.16
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow transparent'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1367P)^2^+1.2939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.1901
_reflns_number_gt                4501
_reflns_number_total             4869
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo5b00335_si_002.cif
_cod_data_source_block           ps718c_2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036171