Diastereoselective Hydroxylation of 6-Substituted Piperidin-2-ones. An Efficient Synthesis of (2S,5R)-5-Hydroxylysine and Related α-Amino Acids
J. Marin; C. Didierjean; A. Aubry; J.-P. Briand; G. Guichard; Journal of Organic Chemistry 67 (2002) 8440–8449; doi:10.1021/jo025950c

data_4022246
_publ_section_title
;
 Diastereoselective Hydroxylation of 6-Substituted Piperidin-2-ones.
 An Efficient Synthesis of (2S,5R)-5-Hydroxylysine
 and Related \a-Amino Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8440
_journal_page_last               8449
_journal_paper_doi               10.1021/jo025950c
_journal_volume                  67
_journal_year                    2002
_chemical_formula_sum            'C15 H25 N O5'
_chemical_formula_weight         299.36
_chemical_name_common
;
N-acylated-piperidin-2-one
;
_chemical_name_systematic
; 
di(tert-butyl)-(2S)-6-oxotetrahydro-1,2(2H)-pyridinedicarboxylate 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9780(4)
_cell_length_b                   10.5680(8)
_cell_length_c                   27.154(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1715.5(2)
_computing_data_reduction        DENZO-SMN
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.900
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_device_type  'Kappa CCD Nonius B.V.'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            3693
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             648
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.036(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0629
_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^)+(0.1053P)^2^+0.4137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1905
_reflns_number_gt                1904
_reflns_number_total             2485
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo025950c-3_s2_1.cif
_cod_data_source_block           compound6a
_cod_database_code               4022246