Diastereoselective synthesis of chiral 3-substituted isoindolinones <i>via</i> rhodium(III)-catalyzed oxidative C-H olefination/annulation.
Li, Xue-Hong; Gong, Jun-Fang; Song, Mao-Ping; Organic & biomolecular chemistry 19 (2021) 5876–5887; doi:10.1039/d1ob00656h

data_7158117
_publ_section_title
;
 Diastereoselective synthesis of chiral 3-substituted isoindolinones
 <i>via</i> rhodium(III)-catalyzed oxidative C-H olefination/annulation.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5876
_journal_page_last               5887
_journal_paper_doi               10.1039/d1ob00656h
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H21 N O4 S'
_chemical_formula_sum            'C16 H21 N O4 S'
_chemical_formula_weight         323.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2019-12-14 deposited with the CCDC.	2021-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.944(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4481(4)
_cell_length_b                   10.3898(5)
_cell_length_c                   17.9970(9)
_cell_measurement_reflns_used    4229
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5080
_cell_measurement_theta_min      4.2560
_cell_volume                     1753.70(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
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_diffrn_measurement_details
;
  1 omega -102.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000    0.0000 84

  2 omega  -37.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  3 omega   37.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 26

  4 omega   10.00   51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 41

  5 omega   -1.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 31

  6 omega   17.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -120.0000 81

  7 omega   69.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  8 omega   70.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -30.0000 33

  9 omega   28.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   30.0000 30

 10 omega   56.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 26

 11 omega   15.00   50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 35

 12 omega   50.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 27

 13 omega   10.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   60.0000 46

 14 omega   18.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 27

 15 omega   57.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 16 omega   14.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 17 omega   47.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 18 omega    3.00   40.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 19 omega   44.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 20 omega  -31.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 21 omega   72.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 22 omega   57.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   30.0000 26

 23 omega   69.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 40

 24 omega   79.00  112.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 33

 25 omega   82.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 25

 26 omega   89.00  114.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 25

 27 omega   83.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 26

 28 omega   89.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 26

 29 omega   88.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 27

 30 omega  117.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 59

 31 omega   91.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 26

 32 omega   82.00  118.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 36

 33 omega   40.00  100.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 60

 34 omega   79.00  104.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 25

 35 omega   64.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 25

 36 omega   88.00  167.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 79

 37 omega  126.00  158.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 32

 38 omega   83.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 26

 39 omega  120.00  156.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 36

 40 omega  143.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 33

 41 omega   79.00  104.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 25

 42 omega   79.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 26

 43 omega   38.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 68

 44 omega   88.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 25

 45 omega   89.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 26

 46 omega  144.00  171.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 27

 47 omega   38.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 48 omega   82.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 26

 49 omega   79.00  104.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 50 omega   89.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 26

 51 omega  121.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 55

 52 omega   88.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 53 omega  124.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 54 omega   47.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 55 omega   84.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1572883000
_diffrn_orient_matrix_UB_12      0.0177957000
_diffrn_orient_matrix_UB_13      0.0323605000
_diffrn_orient_matrix_UB_21      0.0366156000
_diffrn_orient_matrix_UB_22      0.0393716000
_diffrn_orient_matrix_UB_23      -0.0779994000
_diffrn_orient_matrix_UB_31      -0.0298466000
_diffrn_orient_matrix_UB_32      0.1418417000
_diffrn_orient_matrix_UB_33      0.0175474000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14681
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.715
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1585 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5731
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0912P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.823
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                4637
_reflns_number_total             5731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00656h2.cif
_cod_data_source_block           201804235
_cod_depositor_comments
'Adding full bibliography for 7158117--7158118.cif.'
_cod_original_cell_volume        1753.69(14)
_cod_database_code               7158117
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.789
_shelx_estimated_absorpt_t_min   0.728
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11'-C12'
 1.55 with sigma of 0.02
 C17-C18
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C11') = Uanis(C17)
Uanis(C12') = Uanis(C18)
4. Others
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=1-FVAR(1)
 Sof(C11')=Sof(H11A)=Sof(H11B)=Sof(C12')=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C8'(H8')
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11C,H11D), C9'(H9'A,H9'B), C11'(H11A,H11B), C17(H17A,H17B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4')
5.d Idealised Me refined as rotating group:
 C12(H12D,H12E,H12F), C14(H14D,H14E,H14F), C15(H15D,H15E,H15F), C16(H16D,H16E,
 H16F), C12'(H12A,H12B,H12C), C14'(H14A,H14B,H14C), C15'(H15A,H15B,H15C),
 C16'(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'