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_4102814
_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_formula_moiety         'C18 H26 B Br O4'
_chemical_formula_sum            'C18 H26 B Br O4'
_chemical_formula_weight         397.11
_chemical_melting_point          ?
_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                 102.0810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0774(2)
_cell_length_b                   17.1476(3)
_cell_length_c                   20.9494(4)
_cell_measurement_reflns_used    29152
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.22
_cell_volume                     3891.22(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide \w and \f exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            94552
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_T_max  0.8152
_exptl_absorpt_correction_T_min  0.4828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.019(3)
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     910
_refine_ls_number_reflns         17164
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.6285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0709
_reflns_number_gt                16022
_reflns_number_total             17164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja104777u_si_005.cif
_cod_data_source_block           C18H26BBrO4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4102814