Design and Synthesis of WJ-Phos, and Application in Cu-Catalyzed Enantioselective Boroacylation of 1,1-Disubstituted Allenes
Han, Jie; Zhou, Wei; Zhang, Pei-Chao; Wang, Huamin; Zhang, Ronghua; Wu, Hai-Hong; Zhang, Junliang; ACS Catalysis 9 (2019) 6890–; doi:10.1021/acscatal.9b02080

data_4514639
_publ_section_title
;
 Design and Synthesis of WJ-Phos, and Application in Cu-Catalyzed
 Enantioselective Boroacylation of 1,1-Disubstituted Allenes
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              6890
_journal_paper_doi               10.1021/acscatal.9b02080
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H29 B O3'
_chemical_formula_sum            'C24 H29 B O3'
_chemical_formula_weight         376.28
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.85340(10)
_cell_length_b                   12.68130(10)
_cell_length_c                   18.9601(2)
_cell_measurement_reflns_used    36274
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2870
_cell_measurement_theta_min      4.1730
_cell_volume                     2128.70(4)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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 -39.00   1.00    1.00    --    0.00 -69.00 175.00   47
  2  \w    -22.00  16.00   1.00    1.00    --    0.00 -69.00 175.00   38
  3  \w     47.00 123.00   1.00    1.00    --   95.80 -69.00 175.00   76
  4  \w     68.00  93.00   1.00    1.00    --   95.80  69.00 -51.00   25
  5  \w    -27.00  16.00   1.00    1.00    --    0.00  69.00 -51.00   43
  6  \w    -20.00  19.00   1.00    1.00    --    0.00 -38.00 -90.00   39
  7  \w    -23.00  29.00   1.00    1.00    --    0.00  19.00 150.00   52
  8  \w    -16.00  11.00   1.00    1.00    --    0.00 -77.00  60.00   27
  9  \w     26.00  63.00   1.00    1.00    --    0.00  57.00  90.00   37
 10  \w    -56.00 -27.00   1.00    1.00    --    0.00 -57.00  90.00   29
 11  \w    -26.00   0.00   1.00    1.00    --    0.00 -57.00  90.00   26
 12  \w     34.00  85.00   1.00    1.00    --    0.00  19.00 150.00   51
 13  \w    -23.00  13.00   1.00    1.00    --    0.00  57.00  90.00   36
 14  \w    -19.00  54.00   1.00    1.00    --    0.00  38.00  30.00   73
 15  \w    -22.00  43.00   1.00    1.00    --    0.00  19.00 -60.00   65
 16  \w     64.00  89.00   1.00    1.00    --    0.00  38.00  30.00   25
 17  \w    -23.00  24.00   1.00    1.00    --    0.00  57.00   0.00   47
 18  \w    -17.00  85.00   1.00    1.00    --    0.00  38.00-180.00  102
 19  \w    -86.00 -30.00   1.00    1.00    --    0.00 -77.00  60.00   56
 20  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 21  \w     68.00  93.00   1.00    1.00    --   95.80  69.00  98.53   25
 22  \w    114.00 185.00   1.00    1.00    --   95.80  65.00 -13.89   71
 23  \w    126.00 154.00   1.00    1.00    --   95.80  77.00   0.00   28
 24  \w     65.00  93.00   1.00    1.00    --   95.80  77.00   0.00   28
 25  \w     69.00 100.00   1.00    1.00    --   95.80  65.00 -13.89   31
 26  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-120.00   26
 27  \w      7.00  42.00   1.00    1.00    --   95.80 -82.00  30.00   35
 28  \w     52.00 128.00   1.00    1.00    --   95.80 -82.00  30.00   76
 29  \w     71.00 184.00   1.00    1.00    --   95.80  61.00 120.00  113
 30  \w     71.00 103.00   1.00    1.00    --   95.80  58.00 -16.73   32
 31  \w     72.00 122.00   1.00    1.00    --   95.80  57.00  81.96   50
 32  \w    131.00 169.00   1.00    1.00    --   95.80  57.00  81.96   38
 33  \w     75.00 108.00   1.00    1.00    --   95.80  45.00 -30.00   33
 34  \w     49.00 128.00   1.00    1.00    --   95.80 -82.00-120.00   79
 35  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 36  \w     73.00 113.00   1.00    1.00    --   95.80  61.00  60.00   40
 37  \w    101.00 185.00   1.00    1.00    --   95.80  79.00-166.82   84
 38  \w     64.00  89.00   1.00    1.00    --   95.80  79.00-166.82   25
 39  \w     68.00 176.00   1.00    1.00    --   95.80  68.00  92.91  108
 40  \w     75.00 117.00   1.00    1.00    --   95.80  45.00 -60.00   42
 41  \w     65.00  94.00   1.00    1.00    --   95.80  77.00 120.00   29
 42  \w     71.00 108.00   1.00    1.00    --   95.80  61.00-120.00   37
 43  \w     75.00 102.00   1.00    1.00    --   95.80  61.00-180.00   27
 44  \w     68.00  93.00   1.00    1.00    --   95.80  70.00-112.10   25
 45  \w     66.00  91.00   1.00    1.00    --   95.80  74.00 116.95   25
 46  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 47  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-114.46   26
 48  \w    122.00 174.00   1.00    1.00    --   95.80  61.00  60.00   52
 49  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 50  \w     65.00 184.00   1.00    1.00    --   95.80  76.00 140.94  119
 51  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 52  \w     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 53  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 54  \w     75.00 180.00   1.00    1.00    --   95.80  45.00  30.00  105
 55  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 56  \w     71.00 101.00   1.00    1.00    --   95.80  61.00-150.00   30
 57  \w     68.00 136.00   1.00    1.00    --   95.80  70.00  30.96   68
 58  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 59  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 60  \w    108.00 184.00   1.00    1.00    --   95.80  82.00 -60.00   76
 61  \w     67.00  93.00   1.00    1.00    --   95.80  71.00-148.89   26
 62  \w    104.00 185.00   1.00    1.00    --   95.80  71.00-148.89   81
 63  \w     66.00  92.00   1.00    1.00    --   95.80  78.00 -80.79   26
 64  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 65  \w    119.00 145.00   1.00    1.00    --   95.80  45.00 -30.00   26
 66  \w     71.00 182.00   1.00    1.00    --   95.80  58.00-103.92  111
 67  \w     50.00 128.00   1.00    1.00    --   95.80 -82.00 -30.00   78
 68  \w    131.00 185.00   1.00    1.00    --   95.80  82.00-120.00   54
 69  \w    130.00 182.00   1.00    1.00    --   95.80  78.00 -80.79   52
 70  \w     63.00 106.00   1.00    1.00    --   95.80 -82.00 150.00   43
 71  \w     65.00 115.00   1.00    1.00    --   95.80  77.00-180.00   50
;
_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      -0.0392193000
_diffrn_orient_matrix_UB_12      -0.1095776000
_diffrn_orient_matrix_UB_13      -0.0299094000
_diffrn_orient_matrix_UB_21      -0.1022786000
_diffrn_orient_matrix_UB_22      0.0518835000
_diffrn_orient_matrix_UB_23      -0.0558060000
_diffrn_orient_matrix_UB_31      0.1352179000
_diffrn_orient_matrix_UB_32      0.0074822000
_diffrn_orient_matrix_UB_33      -0.0509257000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1328
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            52124
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.537
_diffrn_reflns_theta_min         4.194
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38962
_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    1.174
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(8)
_refine_ls_extinction_coef       0.0070(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0358P)^2^+0.3812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4259
_reflns_number_total             4319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02080_si_003.cif
_cod_data_source_block           exp_461
_cod_database_code               4514639
_shelx_shelxl_version_number     2016/6
_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.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12)
2.c X=CH2 refined with riding coordinates:
 C18(H18a,H18b)
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C20(H20a,H20b,H20c), C21(H21a,H21b,H21c), C23(H23a,H23b,
 H23c), C24(H24a,H24b,H24c)
;
_shelx_res_checksum              49636
_shelx_hkl_checksum              54259
_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 5.493
_oxdiff_exptl_absorpt_empirical_full_min 0.226