Silver-Assisted, Iridium-Catalyzed Allylation of Bis[(pinacolato)boryl]methane Allows the Synthesis of Enantioenriched Homoallylic Organoboronic Esters
Zhan, Miao; Li, Ren-Zhe; Mou, Ze-Dong; Cao, Chao-Guo; Liu, Jie; Chen, Yuan-Wei; Niu, Dawen; ACS Catalysis 6 (2016) 3381–; doi:10.1021/acscatal.6b00719

data_4513871
_publ_section_title
;
 Silver-Assisted, Iridium-Catalyzed Allylation of
 Bis[(pinacolato)boryl]methane Allows the Synthesis of Enantioenriched
 Homoallylic Organoboronic Esters
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              3381
_journal_paper_doi               10.1021/acscatal.6b00719
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H26 B N O2'
_chemical_formula_sum            'C19 H26 B N O2'
_chemical_formula_weight         311.21
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.164(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.86010(19)
_cell_length_b                   17.3729(3)
_cell_length_c                   10.9482(3)
_cell_measurement_reflns_used    9683
_cell_measurement_temperature    290.85(10)
_cell_measurement_theta_max      72.2760
_cell_measurement_theta_min      4.3410
_cell_volume                     1748.92(7)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.85(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -34.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240  -38.0000  120.0000 89

  2 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240 -125.0000 -120.0000 66

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240  -99.0000    0.0000 74

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240  -99.0000   30.0000 74

  5 omega  -34.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240  -38.0000   30.0000 89

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240  -99.0000   90.0000 74

  7 omega  -32.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240  -77.0000 -120.0000 94

  8 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240   38.0000  -30.0000 88

  9 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240   57.0000    0.0000 84

 10 omega  -32.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240  -57.0000 -150.0000 84

 11 omega   39.00  109.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 12 omega   38.00   91.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 13 omega   40.00   98.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 14 omega   90.00  175.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

 15 omega   91.00  176.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 16 omega   40.00   98.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 17 omega   40.00   98.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 18 omega   90.00  175.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

 19 omega   40.00  135.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 95

 20 omega   38.00   91.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 21 omega   38.00  116.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 22 omega   39.00  109.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 23 omega   90.00  175.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

 24 omega   39.00  109.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 25 omega   38.00   91.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 26 omega   70.00  178.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108

 27 omega   39.00  109.00   1.0000    1.6700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 28 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240   57.0000   90.0000 84

 29 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240   77.0000 -150.0000 94

 30 omega  -32.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240  -57.0000  -60.0000 84

 31 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240   77.0000   30.0000 94

 32 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6240   77.0000  150.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0696858000
_diffrn_orient_matrix_UB_12      0.0752117000
_diffrn_orient_matrix_UB_13      -0.0689953000
_diffrn_orient_matrix_UB_21      0.0335893000
_diffrn_orient_matrix_UB_22      0.0388575000
_diffrn_orient_matrix_UB_23      0.1342153000
_diffrn_orient_matrix_UB_31      0.1485339000
_diffrn_orient_matrix_UB_32      0.0264920000
_diffrn_orient_matrix_UB_33      -0.0012610000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18591
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         4.809
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80626
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6230
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0486
_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^)+(0.0950P)^2^+0.2700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6068
_reflns_number_total             6230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00719_si_002.cif
_cod_data_source_block           xnkd-zm-7-287-110k
_cod_depositor_comments          'Adding full bibliography for 4513871.cif.'
_cod_original_cell_volume        1748.93(6)
_cod_database_code               4513871
_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 Ternary CH refined with riding coordinates:
 C00P(H00P), C00U(H00)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00V,H00W), C00W(H00I,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00R), C00G(H00G), C00H(H00H), C00I(H00X),
 C00J(H00J), C00L(H00L), C00M(H00M), C00O(H00Y), C00X(H1AA), C013(H013)
2.d Idealised Me refined as rotating group:
 C00E(H00S,H00T,H00U), C00R(H00Z,H,HA), C00T(H00D,H00E,H00F), C00V(H0AA,HB,HC),
  C00Y(H00N,H00O,H00Q), C012(H01A,H01B,H01C), C014(H01J,H01K,H01L), C018(H01D,
 H01E,H01F), C019(H01O,H01P,H01Q), C01A(H01G,H01H,H01I)
;
_shelx_res_checksum              95975
_shelx_hkl_checksum              1978
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-29
_olex2_submission_special_instructions 'No special instructions were received'