Synthesis of α-trifluoromethyl-β-lactams <i>via</i> a copper-catalyzed Kinugasa reaction of nitrones with 3,3,3-trifluoropropyne and their defluorination.
Chen, Shouxiong; Yang, Peiqi; Hong, Biqiong; Yang, Fafu; Weng, Zhiqiang; Organic & biomolecular chemistry 24 (2026) 1908–1914; doi:10.1039/d5ob01913c

data_7160946
_publ_section_title
;
 Synthesis of &#x3b1;-trifluoromethyl-&#x3b2;-lactams <i>via</i> a
 copper-catalyzed Kinugasa reaction of nitrones with
 3,3,3-trifluoropropyne and their defluorination.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1908
_journal_page_last               1914
_journal_paper_doi               10.1039/d5ob01913c
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2nxl6d
_audit_creation_date             2025-06-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-08-27 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.500(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8464(7)
_cell_length_b                   21.4478(17)
_cell_length_c                   11.1795(10)
_cell_measurement_reflns_used    3020
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0850
_cell_measurement_theta_min      2.7010
_cell_volume                     1813.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     62.00  93.00   0.50    9.00    --    5.00  55.00-120.00   62
  2  \w    -64.00  79.00   0.50    9.00    --   -9.30  55.00   0.00  286
  3  \w     23.00  66.00   0.50    9.00    --   -9.30  43.00 120.00   86
  4  \w    -94.00 -26.00   0.50    9.00    --   -9.30  43.00 120.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0388701000
_diffrn_orient_matrix_UB_12      -0.0095179000
_diffrn_orient_matrix_UB_13      -0.0475617000
_diffrn_orient_matrix_UB_21      -0.0010366000
_diffrn_orient_matrix_UB_22      -0.0314068000
_diffrn_orient_matrix_UB_23      0.0195075000
_diffrn_orient_matrix_UB_31      -0.0853710000
_diffrn_orient_matrix_UB_32      -0.0039798000
_diffrn_orient_matrix_UB_33      -0.0411494000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13503
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.594
_diffrn_reflns_theta_min         1.899
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.0950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3160
_refine_ls_wR_factor_ref         0.3549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2289
_reflns_number_total             4222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01913c2.cif
_cod_data_source_block           20250226-ysh
_cod_depositor_comments
'Adding full bibliography for 7160944--7160947.cif.'
_cod_database_code               7160946
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.995
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C00M-C00K
 1.52 with sigma of 0.001
 C00D-O003
 1.42 with sigma of 0.001
 O003-C00K
 1.42 with sigma of 0.001
 C00G-C00O
 1.5 with sigma of 0.001
3. Rigid bond restraints
 O003, C00D
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C00G, C00D
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C00M, C00K
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C00O) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C00M) \\sim Ueq, Uanis(C00K) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C008(H008), C00A(H00A)
5.b Secondary CH2 refined with riding coordinates:
 C00K(H00B,H00D)
5.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C00C(H00C), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00J(H00J)
5.d Idealised Me refined as rotating group:
 C00L(H00G,H00K,H00L), C00M(H00M,H00N,H00O), C00N(H00P,H00Q,H00R), C00O(H00S,
 H00T,H00U)
;
_shelx_res_checksum              93830
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.634