Cu-Catalyzed Asymmetric Hydroboration of Naphthylallylic Compounds for Enantioselective Synthesis of Chiral Boronates.
Han, Suna; Shen, Xin; Kong, Duanyang; Zi, Guofu; Hou, Guohua; Zhang, Jiaxin; The Journal of organic chemistry 84 (2019) 4318–4329; doi:10.1021/acs.joc.9b00289

data_4034292
_publ_section_title
;
 Cu-Catalyzed Asymmetric Hydroboration of Naphthylallylic Compounds for
 Enantioselective Synthesis of Chiral Boronates.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4318
_journal_page_last               4329
_journal_paper_doi               10.1021/acs.joc.9b00289
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H38 B N O4'
_chemical_formula_sum            'C27 H38 B N O4'
_chemical_formula_weight         451.39
_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
_audit_creation_date             2018-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.94420(10)
_cell_length_b                   12.51520(10)
_cell_length_c                   18.8958(2)
_cell_measurement_reflns_used    16026
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.9330
_cell_measurement_theta_min      4.6490
_cell_volume                     2588.14(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -41.00 -16.00   1.00    1.00    --  -41.49 -57.00 -90.00   25
  2  \w   -122.00 -65.00   1.00    1.00    --  -41.49 -19.00-150.00   57
  3  \w    -93.00 -14.00   1.00    1.00    --  -41.49 -57.00-180.00   79
  4  \w    -64.00 -37.00   1.00    1.00    --  -41.49 -37.00 -60.00   27
  5  \w    -40.00  -7.00   1.00    1.00    --  -41.49 -19.00-150.00   33
  6  \w   -103.00 -23.00   1.00    1.00    --  -41.49 -77.00 -90.00   80
  7  \w    -62.00 -17.00   1.00    1.00    --  -41.49 -77.00 -60.00   45
  8  \w    -72.00 -47.00   1.00    1.00    --  -41.49 -37.00-180.00   25
  9  \w    -80.00  -2.00   1.00    1.00    --  -41.49 125.00-180.00   78
 10  \w    -70.00 -44.00   1.00    1.00    --  -41.49 -57.00 -60.00   26
 11  \w    -34.00  35.00   1.00    1.00    --   41.49 -77.00 150.00   69
 12  \w     76.00 102.00   1.00    2.00    --  104.69  61.00 -30.00   26
 13  \w     72.00 100.00   1.00    2.00    --  104.69  77.00-150.00   28
 14  \w     22.00  50.00   1.00    2.00    --  104.69 -94.00 -90.00   28
 15  \w     72.00  98.00   1.00    2.00    --  104.69  77.00-120.00   26
 16  \w    119.00 177.00   1.00    2.00    --  104.69  61.00   0.00   58
 17  \w     31.00 101.00   1.00    2.00    --  104.69-125.00 150.00   70
 18  \w     53.00 109.00   1.00    2.00    --  104.69 -94.00   0.00   56
 19  \w     72.00  98.00   1.00    2.00    --  104.69  77.00 -60.00   26
 20  \w     77.00 105.00   1.00    2.00    --  104.69  61.00   0.00   28
 21  \w     76.00 102.00   1.00    2.00    --  104.69  61.00-120.00   26
 22  \w    108.00 171.00   1.00    2.00    --  104.69  77.00 -30.00   63
 23  \w     76.00 102.00   1.00    2.00    --  104.69  61.00 -60.00   26
 24  \w    105.00 168.00   1.00    2.00    --  104.69 118.00 -78.00   63
 25  \w     72.00  97.00   1.00    2.00    --  104.69  77.00-180.00   25
 26  \w    110.00 176.00   1.00    2.00    --  104.69  77.00 -90.00   66
 27  \w     80.00 123.00   1.00    2.00    --  104.69  45.00 -30.00   43
 28  \w     80.00 164.00   1.00    2.00    --  104.69  45.00-120.00   84
 29  \w     79.00 116.00   1.00    2.00    --  104.69  45.00 -90.00   37
 30  \w     79.00 106.00   1.00    2.00    --  104.69  45.00 -60.00   27
 31  \w     72.00  98.00   1.00    2.00    --  104.69  77.00 -30.00   26
 32  \w    128.00 164.00   1.00    2.00    --  104.69  61.00-150.00   36
 33  \w     72.00  97.00   1.00    2.00    --  104.69  77.00 -90.00   25
 34  \w     76.00 102.00   1.00    2.00    --  104.69  61.00-150.00   26
 35  \w     80.00 105.00   1.00    2.00    --  104.69  45.00   0.00   25
 36  \w     70.00 105.00   1.00    2.00    --  104.69 -94.00 -90.00   35
 37  \w     76.00 103.00   1.00    2.00    --  104.69  61.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1204024000
_diffrn_orient_matrix_UB_12      -0.0020854000
_diffrn_orient_matrix_UB_13      0.0422126000
_diffrn_orient_matrix_UB_21      -0.0716255000
_diffrn_orient_matrix_UB_22      0.0200154000
_diffrn_orient_matrix_UB_23      0.0689405000
_diffrn_orient_matrix_UB_31      -0.0138097000
_diffrn_orient_matrix_UB_32      -0.1214176000
_diffrn_orient_matrix_UB_33      0.0106602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23814
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.092
_diffrn_reflns_theta_min         4.237
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.158
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0305P)^2^+0.5338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                4791
_reflns_number_total             5029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00289_si_002.cif
_cod_data_source_block           20180911d
_cod_database_code               4034292
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1B1N1O1
_reflns_odcompleteness_completeness 99.96
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C15(H15)
2.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              16836
_shelx_hkl_checksum              616
_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 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.789