Enantioselective Synthesis of Boron-Substituted Quaternary Carbons by NHC-Cu-Catalyzed Boronate Conjugate Additions to Unsaturated Carboxylic Esters, Ketones, or Thioesters
Jeannette M. O'Brien; Kang-sang Lee; Amir H. Hoveyda; Journal of the American Chemical Society 132 (2010) 10630–10633; doi:10.1021/ja104777u

data_4102813
_publ_section_title
;
 Enantioselective Synthesis of Boron-Substituted Quaternary Carbons by
 NHC-Cu-Catalyzed Boronate Conjugate Additions to Unsaturated Carboxylic
 Esters, Ketones, or Thioesters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10630
_journal_page_last               10633
_journal_paper_doi               10.1021/ja104777u
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        syntheszed
_chemical_formula_moiety         'C22 H29 B O4'
_chemical_formula_sum            'C22 H29 B O4'
_chemical_formula_weight         369.27
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.885(2)
_cell_angle_beta                 72.9090(10)
_cell_angle_gamma                71.408(2)
_cell_formula_units_Z            1
_cell_length_a                   6.2174(3)
_cell_length_b                   9.1621(5)
_cell_length_c                   10.3772(6)
_cell_measurement_reflns_used    9204
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.0152
_cell_measurement_theta_min      4.6645
_cell_volume                     511.84(5)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker SMART DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9561
_diffrn_reflns_theta_full        67.01
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_min         4.66
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS '
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.8807
_exptl_absorpt_correction_T_min  0.8371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             199
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.064
_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_coef       0.102(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.0461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                3198
_reflns_number_total             3198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja104777u_si_004.cif
_cod_data_source_block           C22H29BO4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               4102813