Palladium-catalyzed enantioselective umpolung allylation of amido-tethered allylic carbonates with isatin-derived ketimines.
Wang, Lan; Lu, Mengxi; Li, Kuan; Yang, Sen; Wang, Lei; Guo, Hongchao; Chemical communications (Cambridge, England) 60 (2024) 3729–3732; doi:10.1039/d4cc00060a

data_7132800
_publ_section_title
;
 Palladium-catalyzed enantioselective umpolung allylation of
 amido-tethered allylic carbonates with isatin-derived ketimines.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3729
_journal_page_last               3732
_journal_paper_doi               10.1039/d4cc00060a
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C33 H28 F3 N3 O2'
_chemical_formula_sum            'C33 H28 F3 N3 O2'
_chemical_formula_weight         555.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2023-07-05 deposited with the CCDC.	2024-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.24050(10)
_cell_length_b                   13.6044(3)
_cell_length_c                   25.8384(5)
_cell_measurement_reflns_used    15548
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3380
_cell_measurement_theta_min      3.4050
_cell_volume                     2896.67(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -130.00 -32.00   0.50    0.20    -- -105.03  80.00-114.00  196
  2  \w    -71.00 -32.00   0.50    0.20    -- -105.03  61.00 -60.00   78
  3  \w    -67.00 -36.00   0.50    0.20    -- -105.03  61.00  90.00   62
  4  \w   -177.00 -91.00   0.50    0.20    -- -105.03 -41.00 -80.00  172
  5  \w    -26.00  29.00   0.50    0.05    --  -46.53  19.00 -30.00  110
  6  \w    -72.00  26.00   0.50    0.05    --  -46.53  80.00-114.00  196
  7  \w    -26.00  29.00   0.50    0.05    --  -46.53  19.00-150.00  110
  8  \w     59.00 100.00   0.50    0.20    --  108.16 -95.00  60.00   82
  9  \w     35.00  71.00   0.50    0.20    --  108.16 -61.00 -60.00   72
 10  \w     95.00 173.00   0.50    0.20    --  108.16  30.00-150.00  156
 11  \w     74.00 120.00   0.50    0.05    --   49.66 125.00  90.00   92
 12  \w     72.00 121.00   0.50    0.05    --   49.66 127.00 129.00   98
 13  \w     72.00 178.00   0.50    0.20    --  108.16 127.00 129.00  212
 14  \w    -25.00   0.00   0.50    0.05    --   48.99 -38.00   0.00   50
 15  \w    -21.00  57.00   0.50    0.05    --   48.99 -77.00 120.00  156
 16  \w      1.00  26.00   0.50    0.05    --   48.99 -19.00 -60.00   50
 17  \w    -12.00  15.00   0.50    0.05    --   48.99 -38.00  60.00   54
 18  \w      7.00  43.00   0.50    0.05    --   48.99 -38.00   0.00   72
 19  \w   -109.00 -79.00   0.50    0.20    -- -105.45 125.00-150.00   60
 20  \w   -169.00-143.00   0.50    0.20    -- -105.45 -15.00   0.00   52
 21  \w    -65.00 -38.00   0.50    0.20    -- -105.45 125.00 -90.00   54
 22  \w   -150.00 -91.00   0.50    0.20    -- -105.45 -45.00 120.00  118
 23  \w   -133.00-107.00   0.50    0.20    -- -105.45 -15.00   0.00   52
 24  \w   -109.00 -72.00   0.50    0.20    -- -105.45 125.00 -90.00   74
 25  \w   -126.00 -99.00   0.50    0.20    -- -105.45 -45.00  30.00   54
 26  \w    -67.00 -39.00   0.50    0.20    -- -105.45 125.00-150.00   56
 27  \w   -163.00-132.00   0.50    0.20    -- -105.45 -45.00  30.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1597429000
_diffrn_orient_matrix_UB_12      0.0587326000
_diffrn_orient_matrix_UB_13      0.0027487000
_diffrn_orient_matrix_UB_21      -0.0135612000
_diffrn_orient_matrix_UB_22      -0.0034143000
_diffrn_orient_matrix_UB_23      -0.0594253000
_diffrn_orient_matrix_UB_31      -0.0963017000
_diffrn_orient_matrix_UB_32      -0.0967383000
_diffrn_orient_matrix_UB_33      0.0037941000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23629
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.575
_diffrn_reflns_theta_max         66.575
_diffrn_reflns_theta_min         4.720
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1754 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0840P)^2^+0.1840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1293
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4504
_reflns_number_total             5083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00060a2.cif
_cod_data_source_block           1-block_auto
_cod_depositor_comments          'Adding full bibliography for 7132800.cif.'
_cod_database_code               7132800
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         CHON
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.861
_diffrn_oxdiff_digest_frames
;
01cffd2d7ae102b0b17999a25f7f8e9074016364a35
;
_diffrn_oxdiff_digest_hkl
;
0168abe15dfbeb0477a6134bfc8a6185a864a8
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C25(H25), C7(H7), C9(H9), C24(H24), C22(H22), C15(H15), C11(H11),
 C23(H23), C6(H6), C13(H13), C12(H12), C3(H3), C14(H14), C33(H33), C5(H5),
 C29(H29), C30(H30), C4(H4), C31(H31), C32(H32)
;
_shelx_res_checksum              86787
_shelx_hkl_checksum              69173
_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 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.522