cis-Dihydroxylated α-Trifluoromethylated N,O-Acetal from l-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of N-Acyliminium Ions
Ben Jamaa, Abdelkhalek; Latrache, Mohammed; Riguet, Emmanuel; Grellepois, Fabienne; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c00801

data_4038612
_publ_section_title
;
 cis-Dihydroxylated \a-Trifluoromethylated N,O-Acetal from l-Tartaric
 Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective
 Pictet-Spengler Cyclization of N-Acyliminium Ions
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00801
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H18 F3 N O4'
_chemical_formula_weight         345.31
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   8.260(5)
_cell_length_b                   10.089(5)
_cell_length_c                   18.565(5)
_cell_measurement_reflns_used    9206
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      74.49
_cell_measurement_theta_min      4.99
_cell_volume                     1547.1(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      101(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34080
_diffrn_reflns_theta_full        74.48
_diffrn_reflns_theta_max         74.48
_diffrn_reflns_theta_min         4.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.191
_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   -0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0233
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.2393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0612
_reflns_number_gt                3115
_reflns_number_total             3173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00801_si_002.cif
_cod_data_source_block           cu_14fg008bis_0m
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4038612