Palladium/Xu-Phos-Catalyzed Asymmetric Carboamination towards Isoxazolidines and Pyrrolidines
Wang, Yuzhuo; Wang, Lei; Chen, Mingjie; Tu, Youshao; Liu, Yu; Zhang, Junliang; Chemical Science  (2021) –; doi:10.1039/D1SC01337H

data_1562387
_publ_section_title
;
 Palladium/Xu-Phos-Catalyzed Asymmetric Carboamination towards
 Isoxazolidines and Pyrrolidines
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01337H
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C42 H68 N O3 P S'
_chemical_formula_sum            'C42 H68 N O3 P S'
_chemical_formula_weight         698.00
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-03 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.71390(10)
_cell_length_b                   14.69290(10)
_cell_length_c                   20.80280(10)
_cell_measurement_reflns_used    51263
_cell_measurement_temperature    100.3(7)
_cell_measurement_theta_max      74.1920
_cell_measurement_theta_min      3.6840
_cell_volume                     4191.70(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.3(7)
_diffrn_detector                 'CCD plate'
_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    -86.00 -61.00   1.00    1.00    --    0.00 -38.00  90.00   25
  2  \w    -16.00  21.00   1.00    1.00    --    0.00  57.00 -30.00   37
  3  \w    -30.00   3.00   1.00    1.00    --    0.00  77.00-180.00   33
  4  \w    -69.00 -22.00   1.00    1.00    --    0.00 -77.00 120.00   47
  5  \w     46.00  84.00   1.00    1.00    --    0.00  57.00 -30.00   38
  6  \w    -87.00 -25.00   1.00    1.00    --    0.00 -77.00  90.00   62
  7  \w     43.00  69.00   1.00    1.00    --    0.00  77.00  90.00   26
  8  \w     35.00  61.00   1.00    1.00    --    0.00  77.00-180.00   26
  9  \w    -88.00  15.00   1.00    1.00    --    0.00 -38.00   0.00  103
 10  \w    -51.00 -23.00   1.00    1.00    --    0.00 -38.00  90.00   28
 11  \w    -14.00  19.00   1.00    1.00    --    0.00 -38.00  90.00   33
 12  \w    -29.00  36.00   1.00    1.00    --    0.00  77.00  90.00   65
 13  \w     -5.00  30.00   1.00    1.00    --    0.00 -77.00  90.00   35
 14  \w    -80.00  19.00   1.00    1.00    --    0.00 -38.00 -60.00   99
 15  \w      5.00  30.00   1.00    1.00    --    0.00 -77.00 120.00   25
 16  \w    -87.00  17.00   1.00    1.00    --    0.00 -38.00-120.00  104
 17  \w     63.00 107.00   1.00    1.00    --   95.80  82.00-140.19   44
 18  \w     70.00 111.00   1.00    1.00    --   95.80  63.00 161.63   41
 19  \w     70.00 103.00   1.00    1.00    --   95.80  63.00 150.80   33
 20  \w    116.00 142.00   1.00    1.00    --   95.80  80.00 -21.36   26
 21  \w     65.00  93.00   1.00    1.00    --   95.80  78.00 -45.45   28
 22  \w     64.00  90.00   1.00    1.00    --   95.80  80.00 -21.36   26
 23  \w     67.00 174.00   1.00    1.00    --   95.80  72.00  -3.72  107
 24  \w     42.00 128.00   1.00    1.00    --   95.80 -82.00  30.00   86
 25  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 26  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 27  \w    118.00 185.00   1.00    1.00    --   95.80  82.00  30.00   67
 28  \w     65.00  91.00   1.00    1.00    --   95.80  82.00-180.00   26
 29  \w    104.00 185.00   1.00    1.00    --   95.80  82.00-180.00   81
 30  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 31  \w     63.00  89.00   1.00    1.00    --   95.80  81.00 -70.07   26
 32  \w     95.00 171.00   1.00    1.00    --   95.80  78.00 165.81   76
 33  \w     65.00  90.00   1.00    1.00    --   95.80  78.00 165.81   25
 34  \w    160.00 185.00   1.00    1.00    --   95.80  78.00 -30.66   25
 35  \w     67.00 175.00   1.00    1.00    --   95.80  72.00 108.32  108
 36  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 37  \w     65.00  90.00   1.00    1.00    --   95.80  76.00  77.58   25
 38  \w     65.00  90.00   1.00    1.00    --   95.80  78.00 -30.66   25
 39  \w     64.00  90.00   1.00    1.00    --   95.80  79.00 141.91   26
 40  \w     53.00 128.00   1.00    1.00    --   95.80 -82.00-120.00   75
 41  \w     75.00 183.00   1.00    1.00    --   95.80  45.00-120.00  108
 42  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 43  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 44  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 45  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 46  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 47  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 48  \w    110.00 184.00   1.00    1.00    --   95.80  82.00 120.00   74
 49  \w     71.00  97.00   1.00    1.00    --   95.80  61.00-150.00   26
 50  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 51  \w     72.00 104.00   1.00    1.00    --   95.80  61.00  30.00   32
 52  \w     71.00 185.00   1.00    1.00    --   95.80  61.00  90.00  114
 53  \w     65.00 111.00   1.00    1.00    --   95.80  77.00 -90.00   46
 54  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 55  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 56  \w     65.00 126.00   1.00    1.00    --   95.80  77.00-120.00   61
 57  \w     63.00 147.00   1.00    1.00    --   95.80  82.00-113.01   84
 58  \w     89.00 127.00   1.00    1.00    --   95.80 -82.00  90.00   38
 59  \w     45.00  78.00   1.00    1.00    --   95.80 -82.00  90.00   33
 60  \w    104.00 176.00   1.00    1.00    --   95.80  76.00  17.31   72
 61  \w     74.00 103.00   1.00    1.00    --   95.80  49.00 -36.63   29
 62  \w    129.00 177.00   1.00    1.00    --   95.80  77.00  60.00   48
 63  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 64  \w     65.00  90.00   1.00    1.00    --   95.80  76.00  17.31   25
 65  \w     75.00 121.00   1.00    1.00    --   95.80  45.00   0.00   46
 66  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 67  \w    111.00 184.00   1.00    1.00    --   95.80  82.00 -90.00   73
 68  \w    144.00 170.00   1.00    1.00    --   95.80  82.00-140.19   26
 69  \w     14.00 127.00   1.00    1.00    --   95.80 -82.00-180.00  113
 70  \w     45.00 104.00   1.00    1.00    --   95.80 -82.00 -30.00   59
 71  \w     67.00  92.00   1.00    1.00    --   95.80  71.00 119.26   25
 72  \w    115.00 172.00   1.00    1.00    --   95.80  81.00 -70.07   57
 73  \w    143.00 178.00   1.00    1.00    --   95.80  58.00  75.30   35
 74  \w     71.00 105.00   1.00    1.00    --   95.80  58.00  75.30   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0861593000
_diffrn_orient_matrix_UB_12      -0.0275085000
_diffrn_orient_matrix_UB_13      -0.0433518000
_diffrn_orient_matrix_UB_21      0.0661966000
_diffrn_orient_matrix_UB_22      0.0075007000
_diffrn_orient_matrix_UB_23      -0.0595440000
_diffrn_orient_matrix_UB_31      0.0284694000
_diffrn_orient_matrix_UB_32      -0.1009647000
_diffrn_orient_matrix_UB_33      0.0073657000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1439
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            102904
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.683
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 3153 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         7476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.7029P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7304
_reflns_number_total             7476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01337h2.cif
_cod_data_source_block           exp_1513
_cod_database_code               1562387
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.761
_shelx_estimated_absorpt_t_min   0.679
_reflns_odcompleteness_completeness 99.98
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C41(H41), C37(H37), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C8(H8A,H8B), C9(H9A,H9B), C18(H18A,H18B), C14(H14A,H14B),
 C17(H17A,H17B), C11(H11A,H11B), C16(H16A,H16B), C10(H10A,H10B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C3(H3), C5(H5), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C27(H27A,H27B,
 H27C), C35(H35A,H35B,H35C), C40(H40A,H40B,H40C), C36(H36A,H36B,H36C), C34(H34A,
 H34B,H34C), C38(H38A,H38B,H38C), C30(H30A,H30B,H30C), C39(H39A,H39B,H39C),
 C32(H32A,H32B,H32C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              81348
_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 2.661
_oxdiff_exptl_absorpt_empirical_full_min 0.391