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_1518270
_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_absolute_configuration unk
_chemical_formula_sum            'C17 H18 Br F3 N2 O5'
_chemical_formula_weight         467.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           18
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_symmetry_space_group_name_Hall  'P 2 2ab'
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_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            8
_cell_length_a                   13.3503(15)
_cell_length_b                   26.402(3)
_cell_length_c                   11.0275(12)
_cell_measurement_temperature    293(2)
_cell_volume                     3886.9(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33633
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    2.174
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.547599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.029(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         8927
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0902P)^2^+1.4209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1986
_reflns_number_gt                3968
_reflns_number_total             8927
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503067g_si_003.cif
_cod_data_source_block           13
_cod_depositor_comments
'Adding full bibliography for 1518270--1518271.cif.'
_cod_original_cell_volume        3886.9(7)
_cod_original_sg_symbol_H-M      P21212
_cod_database_code               1518270