Enantioselective Rhodium-Catalyzed Addition of Arylboronic Acids to Alkenylheteroarenes
Graham Pattison; Guillaume Piraux; Hon Wai Lam; Journal of the American Chemical Society 132 (2010) 14373–14375; doi:10.1021/ja106809p

data_4103318
_publ_contact_author_email       fraser.white@ed.ac.uk
_publ_contact_author_name        'Fraser J. White'
_publ_section_title
;
 Enantioselective Rhodium-Catalyzed Addition of Arylboronic Acids to
 Alkenylheteroarenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14373
_journal_page_last               14375
_journal_paper_doi               10.1021/ja106809p
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        'Graham Pattison'
_chemical_formula_moiety         'C24 H21 F N2 '
_chemical_formula_sum            'C24 H21 F N2'
_chemical_formula_weight         356.43
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.4257(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.84102(9)
_cell_length_b                   9.25426(6)
_cell_length_c                   10.86112(11)
_cell_measurement_reflns_used    16460
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9008
_cell_measurement_theta_min      4.2870
_cell_volume                     938.428(15)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics    Shelxp
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;
  1 omega  -96.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039  -37.0000 -120.0000 81

  2 omega -129.00  -68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039  179.0000 -150.0000 61

  3 omega -116.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039  -37.0000  150.0000 102

  4 omega -113.00  -59.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039 -150.0000    6.0000 54

  5 omega  -55.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039   77.0000 -150.0000 34

  6 omega   47.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0039 -122.0000  168.0000 33

  7 omega   20.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0039   37.0000  120.0000 75

  8 omega   33.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -21.0000  177.0000 40

  9 omega  113.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000  -60.0000 33

 10 omega   87.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 83

 11 omega  131.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 37

 12 omega   92.00  148.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000  150.0000 56

 13 omega   44.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -122.0000  110.0000 74

 14 omega   86.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 90

 15 omega  127.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 49

 16 omega   42.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 26

 17 omega  108.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000 -150.0000 34

 18 omega   42.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 33

 19 omega   64.00  150.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000   90.0000 86

 20 omega   90.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -122.0000  168.0000 27

 21 omega  101.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000  -60.0000 69

 22 omega   82.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 31

 23 omega  104.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 26

 24 omega   58.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000  150.0000 30

 25 omega   34.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 34

 26 omega  103.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000   90.0000 55

 27 omega  135.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000   30.0000 40

 28 omega  135.00  170.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  150.0000   -6.0000 35

 29 omega   88.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000  120.0000 27

 30 omega  118.00  144.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  179.0000  120.0000 26

 31 omega   83.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -121.0000  -72.0000 37

 32 omega -119.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039  -77.0000  150.0000 113

 33 omega -116.00  -57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039 -150.0000  -51.0000 59

 34 omega -119.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039  -77.0000   30.0000 113

 35 omega -119.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039  -77.0000  -90.0000 113

 36 omega -129.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039  179.0000  -90.0000 95

 37 omega -119.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0039  -77.0000    0.0000 113

 38 omega  -36.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0039  -37.0000 -150.0000 102

 39 omega   56.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0039  179.0000 -120.0000 74

 40 omega -140.00  -28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 112

 41 omega -140.00  -28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -30.0000 112

 42 omega -140.00  -28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 112

 43 omega -140.00  -28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 112

 44 omega   79.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 99

 45 omega   85.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   60.0000 93

 46 omega   38.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 39

 47 omega   79.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 99

 48 omega   85.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 93

 49 omega   79.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 99

 50 omega   85.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 93

 51 omega   79.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 99

 52 omega   79.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 99

 53 omega   37.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -121.0000  -72.0000 83

 54 omega   85.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 93

;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20720
_diffrn_reflns_theta_full        76.09
_diffrn_reflns_theta_max         76.09
_diffrn_reflns_theta_min         4.29
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method 'vapour diffusion of Et2O into hexane'
_exptl_crystal_size_max          0.2711
_exptl_crystal_size_mid          0.1793
_exptl_crystal_size_min          0.1263
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.1609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                3791
_reflns_number_total             3884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106809p_si_002.cif
_cod_data_source_block           hl0005
_cod_original_cell_volume        938.428(14)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4103318