Palladium-Catalyzed Amide-Directed Enantioselective Carboboration of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand
Bai, Zibo; Zheng, Sujuan; Bai, Ziqian; Song, Fangfang; Wang, Hao; Peng, Qian; Chen, Gong; He, Gang; ACS Catalysis 9 (2019) 6502–; doi:10.1021/acscatal.9b01350

data_4514802
_publ_section_title
;
 Palladium-Catalyzed Amide-Directed Enantioselective Carboboration of
 Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6502
_journal_paper_doi               10.1021/acscatal.9b01350
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H36 B N3 O3'
_chemical_formula_sum            'C30 H36 B N3 O3'
_chemical_formula_weight         497.43
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.2930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.53990(10)
_cell_length_b                   23.9124(3)
_cell_length_c                   9.10300(10)
_cell_measurement_reflns_used    6633
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      77.3440
_cell_measurement_theta_min      3.7050
_cell_volume                     1390.93(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.944
_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    -24.00  94.00   0.50    0.50    --    5.00  57.00  60.00  236
  2  \w   -140.00 -18.00   0.50    0.50    --  -50.10 -71.00 132.84  244
  3  \w   -199.00 -81.00   0.50    1.00    -- -110.00 -43.00 119.22  236
  4  \w   -199.00 -80.00   0.50    1.00    -- -110.00 -64.00 -28.09  238
  5  \w   -139.00 -21.00   0.50    1.00    -- -110.00  57.00 -90.00  236
  6  \w   -143.00 -21.00   0.50    1.00    -- -110.00  72.00  90.00  244
  7  \w   -143.00 -21.00   0.50    1.00    -- -110.00  72.00 -60.00  244
  8  \w   -141.00 -21.00   0.50    1.00    -- -110.00  38.00-180.00  240
  9  \w   -143.00 -21.00   0.50    1.00    -- -110.00  72.00  30.00  244
 10  \w   -143.00 -43.00   0.50    1.00    -- -110.00  72.00-150.00  200
 11  \w   -199.00 -81.00   0.50    1.00    -- -110.00 -46.00  48.63  236
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0373574000
_diffrn_orient_matrix_UB_12      -0.0592159000
_diffrn_orient_matrix_UB_13      0.0670063000
_diffrn_orient_matrix_UB_21      0.0860629000
_diffrn_orient_matrix_UB_22      0.0253898000
_diffrn_orient_matrix_UB_23      0.1564679000
_diffrn_orient_matrix_UB_31      -0.2221003000
_diffrn_orient_matrix_UB_32      -0.0001389000
_diffrn_orient_matrix_UB_33      0.0319146000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12492
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.992
_diffrn_reflns_theta_min         3.697
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.188
_exptl_crystal_description       prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2061 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_coef       0.0013(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5349
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0860P)^2^+0.0676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.888
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                4960
_reflns_number_total             5349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01350_si_002.cif
_cod_data_source_block           p20190225b
_cod_database_code               4514802
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C30H36N2O3B
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.859
_reflns_odcompleteness_completeness 96.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C7(H7), C8(H8), C9(H9), C17(H17), C20(H20), C21(H21),
  C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              40644
_shelx_hkl_checksum              99573
_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 1.695
_oxdiff_exptl_absorpt_empirical_full_min 0.833