Catalytic Asymmetric Synthesis of Chiral Tertiary Organoboronic Esters through Conjugate Boration of β-Substituted Cyclic Enones
I-Hon Chen; Liang Yin; Wataru Itano; Motomu Kanai; Masakatsu Shibasaki; Journal of the American Chemical Society 131 (2009) 11664–11665; doi:10.1021/ja9045839

data_4104905
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Chiral Tertiary Organoboronic Esters
 through Conjugate Boration of \b-Substituted Cyclic Enones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11664
_journal_page_last               11665
_journal_paper_doi               10.1021/ja9045839
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H14 O2 '
_chemical_formula_sum            'C12 H14 O2'
_chemical_formula_weight         190.24
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.58542(10)
_cell_length_b                   9.57633(17)
_cell_length_c                   18.7881(3)
_cell_measurement_reflns_used    7226
_cell_measurement_temperature    103.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.6
_cell_volume                     1004.93(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11303
_diffrn_reflns_theta_full        68.20
_diffrn_reflns_theta_max         68.20
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       needle
_exptl_crystal_F_000             408.00
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  739 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1845
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.1219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                1649
_reflns_number_total             1845
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja9045839_si_001.cif
_cod_data_source_block           '_090528'
_cod_original_cell_volume        1004.94(3)
_cod_original_formula_sum        'C12 H14 O2 '
_cod_database_code               4104905