Diastereo- and Enantioselective Synthesis of β-Hydroxy-α-Amino Acids: Application to the Synthesis of a Key Intermediate for Lactacystin
Qiong Li; Shao-Bo Yang; Zhihui Zhang; Lei Li; Peng-Fei Xu; Journal of Organic Chemistry 74 (2009) 1627–1631; doi:10.1021/jo8023973

data_4024336
_publ_contact_author_address
;
 State Key Laboratory of Applied Organic Chemistry,
 Lanzhou University, 73000, CHINA
;
_publ_contact_author_email       ' xupf@lzu.edu.cn '
_publ_contact_author_fax         ' 86-931-8915557 '
_publ_contact_author_name        'peng-fei xu'
_publ_contact_author_phone       ' 86-931-8912281 '
_publ_section_title
;
Diastereo- and Enantioselective Synthesis of \b-Hydroxy-\a-Amino Acids:
Application to the Synthesis of a Key Intermediate for Lactacystin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1627
_journal_page_last               1631
_journal_paper_doi               10.1021/jo8023973
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H22 F N O3'
_chemical_formula_sum            'C19 H22 F N O3'
_chemical_formula_weight         331.38
_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                   10.4278(8)
_cell_length_b                   12.2750(10)
_cell_length_c                   13.8915(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1778.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10007
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       0.012(3)
_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   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2962
_reflns_number_total             3488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8023973_si_004.cif
_cod_data_source_block           compd-2f
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_H-M      P2(1)2(1)2(1)
_cod_database_code               4024336