Enantioselective Synthesis of α-Fluoro-β3-amino Esters: Synthesis of Enantiopure, Orthogonally Protected α-Fluoro-β3-lysine
Peter J. Duggan; Martin Johnston; Taryn L. March; Journal of Organic Chemistry 75 (2010) 7365–7372; doi:10.1021/jo101600c

data_4025773
_publ_section_title
;
 Enantioselective Synthesis of \a-Fluoro-\b3-amino Esters: Synthesis of
 Enantiopure, Orthogonally Protected \a-Fluoro-\b3-lysine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7365
_journal_page_last               7372
_journal_paper_doi               10.1021/jo101600c
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration 2S,3S,alphaS
_chemical_formula_sum            'C30 H46 F N O3 Si'
_chemical_formula_weight         515.77
_chemical_melting_point          382
_chemical_name_systematic
;
2S,3S,alphaS-tert-butyl-3-(benzyl(1-phenylethyl)amino)-
5-(tert-butyldimethylsilyloxy)-2-fluoropentanoate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.91840(10)
_cell_length_b                   18.5725(2)
_cell_length_c                   20.6359(3)
_cell_measurement_reflns_used    8806
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      73.1066
_cell_measurement_theta_min      3.1987
_cell_volume                     3034.81(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.0711
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11052
_diffrn_reflns_theta_full        73.26
_diffrn_reflns_theta_max         73.26
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.4801
_exptl_crystal_size_mid          0.2499
_exptl_crystal_size_min          0.1950
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.027(19)
_refine_ls_extinction_coef       0.00046(19)
_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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                5575
_reflns_number_total             5892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101600c_si_002.cif
_cod_data_source_block           tBu-5-TBSO-3-amino-5-fluoro-pentanoate
_cod_database_code               4025773