Enantiopure Trifluoromethylated β3,3-Amino Acids: Synthesis by Asymmetric Reformatsky Reaction with Stable Analogues of TrifluoromethylN-tert-Butanesulfinylketoimines and Incorporation into α/β-Peptides
Fabienne Grellepois; Journal of Organic Chemistry 78 (2013) 1127–1137; doi:10.1021/jo302549v

data_4027926
_publ_contact_author_address
;
Institut de Chimie Mol\'eculaire de Reims 
UMR CNRS 7312
Dr. Fabienne Grellepois
UMR CNRS 7312, boite 44
UFR des Sciences Exactes et Naturelles 
BP 1039 
51687 Reims Cedex 2
;
_publ_contact_author_email       fabienne.grellepois@univ-reims.fr
_publ_contact_author_name        'Grellepois Fabienne'
_publ_section_title
;
 Enantiopure Trifluoromethylated \b3,3-Amino Acids: Synthesis by
 Asymmetric Reformatsky Reaction with Stable Analogues of
 TrifluoromethylN-tert-Butanesulfinylketoimines and Incorporation into
 \a/\b-Peptides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1127
_journal_page_last               1137
_journal_paper_doi               10.1021/jo302549v
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H28 F3 N1 O4 S1'
_chemical_formula_sum            'C19 H28 F3 N O4 S'
_chemical_formula_weight         423.48
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-09-28T15:24:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.000
_cell_angle_beta                 109.129(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   10.188(5)
_cell_length_b                   9.927(5)
_cell_length_c                   11.211(5)
_cell_measurement_reflns_used    5286
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3038
_cell_measurement_theta_min      1.9187
_cell_measurement_wavelength     0.71073
_cell_volume                     1071.2(9)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
        APEXII suite Bruker-AXS
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture with Photon 100 detector'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0238416
_diffrn_orient_matrix_UB_12      -0.0340957
_diffrn_orient_matrix_UB_13      0.0587516
_diffrn_orient_matrix_UB_21      0.069694
_diffrn_orient_matrix_UB_22      0.013246
_diffrn_orient_matrix_UB_23      0.0039358
_diffrn_orient_matrix_UB_31      -0.0018011
_diffrn_orient_matrix_UB_32      0.0613756
_diffrn_orient_matrix_UB_33      0.0319104
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.109
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12656
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.2
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.92362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.2771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.083
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                3025
_reflns_number_total             4352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302549v_si_002.cif
_cod_data_source_block           mo_fg1082_4
_cod_original_sg_symbol_Hall     P2yb
_cod_database_code               4027926