Amide groups switch selectivity: C-H trifluoromethylation of α,β-unsaturated amides and subsequent asymmetric transformation.
Li, Lei; Guo, Jing-Yao; Liu, Xing-Guo; Chen, Su; Wang, Yong; Tan, Bin; Liu, Xin-Yuan; Organic letters 16 (2014) 6032–6035; doi:10.1021/ol503067g

data_1518271
_publ_section_title
;
 Amide groups switch selectivity: C-H trifluoromethylation of
 \a,\b-unsaturated amides and subsequent asymmetric transformation.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6032
_journal_page_last               6035
_journal_paper_doi               10.1021/ol503067g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H8 F3 N O3'
_chemical_formula_sum            'C8 H8 F3 N O3'
_chemical_formula_weight         223.15
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.926(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.9671(4)
_cell_length_b                   5.4454(2)
_cell_length_c                   19.6033(13)
_cell_measurement_reflns_used    2867
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      7.10
_cell_volume                     950.23(8)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5294
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.393
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.350
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.397
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1704
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0963
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'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_ref         0.2951
_reflns_number_gt                804
_reflns_number_total             1704
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol503067g_si_002.cif
_cod_data_source_block           '__liuxinyuan20140519'
_cod_depositor_comments
'Adding full bibliography for 1518270--1518271.cif.'
_cod_database_code               1518271