Totally Selective Synthesis of Enantiopure (3S,5S)- and (3R,5R)-4-Amino-3,5-dihydroxypiperidines from Aminodiepoxides Derived from Serine
José M. Concellón; Ignacio A. Rivero; Humberto Rodríguez-Solla; Carmen Concellón; Estibaly España; Santiago García-Granda; M. R. Díaz; Journal of Organic Chemistry 73 (2008) 6048–6051; doi:10.1021/jo801058c

data_4023593
_publ_section_title
;
 Totally Selective Synthesis of Enantiopure (3S,5S)- and
 (3R,5R)-4-Amino-3,5-dihydroxypiperidines from
 Aminodiepoxides Derived from Serine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6048
_journal_page_last               6051
_journal_paper_doi               10.1021/jo801058c
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C25 H34 N2 O2'
_chemical_formula_sum            'C25 H34 N2 O2'
_chemical_formula_weight         394.54
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_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                 104.001(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4774(2)
_cell_length_b                   19.6666(6)
_cell_length_c                   9.2831(2)
_cell_measurement_reflns_used    2056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0
_cell_measurement_theta_min      2.0
_cell_volume                     1147.43(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4082
_diffrn_reflns_theta_full        68.27
_diffrn_reflns_theta_max         68.27
_diffrn_reflns_theta_min         5.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
Absolute structure was determined without TWIN and BASF in the *.ins file. 
Absolute Configuration of C2 = S
Absolute Configuration of C4 = S
Flack H D (1983), Acta Cryst. A39, 876-881.
The Bijvoet coefficient for the strongest 35 Bijvoet pairs is
 B = 0.514(0.046) and its probability is 1.000
Dirdif (Beurskens et al. 1999)
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.0451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                3769
_reflns_number_total             4082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801058c-File002.cif
_cod_data_source_block           3c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     P2yb
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023593