Diastereoselective Addition of Metal α-Fluoroenolates of Carboxylate Esters to N-tert-Butylsulfinyl Imines: Synthesis of α-Fluoro-β-amino Acids.
Shang, Huaqi; Li, Ya; Li, Xiang; Ren, Xinfeng; The Journal of organic chemistry 80 (2015) 8739–8747; doi:10.1021/acs.joc.5b01574

data_4036330
_publ_section_title
;
 Diastereoselective Addition of Metal \a-Fluoroenolates of Carboxylate
 Esters to N-tert-Butylsulfinyl Imines: Synthesis of \a-Fluoro-\b-amino
 Acids.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8739
_journal_page_last               8747
_journal_paper_doi               10.1021/acs.joc.5b01574
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H30 F N O3 S'
_chemical_formula_weight         419.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5042(2)
_cell_length_b                   15.9784(8)
_cell_length_c                   25.4579(12)
_cell_measurement_reflns_used    1448
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      102.396
_cell_measurement_theta_min      6.944
_cell_volume                     2238.98(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_av_unetI/netI     0.1411
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11464
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_min         3.265
_exptl_absorpt_coefficient_mu    1.544
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
; 
 Flack x determined using 735 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0047(6)
_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   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1431
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                2507
_reflns_number_total             3794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01574_si_003.cif
_cod_data_source_block           cu_dm15382_0m
_cod_database_code               4036330
_shelx_estimated_absorpt_t_min   0.797
_shelx_estimated_absorpt_t_max   0.875
_shelxl_version_number           2013-4
_shelx_res_checksum              91088
_shelx_hkl_checksum              8909