Efficient asymmetric synthesis of trifluoromethylated beta-aminophosphonates and their incorporation into dipeptides
Kostiantyn V. Turcheniuk; Kateryna O. Poliashko; Valery P. Kukhar; Alexander B. Rozhenko; Vadim A. Soloshonok; Alexander E. Sorochinsky; Chem.Commun. 48 (2012) 11519–; doi:10.1039/c2cc36702e

data_7108616
_publ_section_title
;
 Efficient asymmetric synthesis of trifluoromethylated
 beta-aminophosphonates and their incorporation into dipeptides
;
_journal_name_full               Chem.Commun.
_journal_page_first              11519
_journal_paper_doi               10.1039/c2cc36702e
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C11 H23 F3 N O4 P S'
_chemical_formula_weight         353.33
_chemical_melting_point          396
_chemical_name_common
;
Diethyl ((2R)-2-((S)-(tert-butylsulfinyl)amino)-3,3,3-
trifluoropropyl)phosphonate
;
_chemical_name_systematic
;
Diethyl {(2R)-2-[(S)-(tert-butylsulfinyl)amino]-
3,3,3-trifluoropropyl}phosphonate
;
_space_group_IT_number           19
_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                   10.3044(5)
_cell_length_b                   10.6650(5)
_cell_length_c                   16.0642(7)
_cell_measurement_temperature    296(2)
_cell_volume                     1765.40(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17420
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_correction_T_min  0.8587
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorombic
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.5057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2405
_reflns_number_total             3566
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36702e.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7108616