Stereospecific Suzuki-Miyaura Coupling of Chiral α-(Acylamino)benzylboronic Esters with Inversion of Configuration
Toshimichi Ohmura; Tomotsugu Awano; Michinori Suginome; Journal of the American Chemical Society 132 (2010) 13191–13193; doi:10.1021/ja106632j

data_4103135
_publ_contact_author_address
;
Department of Synthetic Chemistry and Biological Chemistry,
Graduate School of Engineering, Kyoto University,
;
_publ_contact_author_email       ' suginome_at_sbchem.kyoto-u.ac.jp '
_publ_contact_author_fax         ' +81-75-383-2722 '
_publ_contact_author_name        ' Michinori Suginome '
_publ_contact_author_phone       ' +81-75-383-2750 '
_publ_section_title
;
 Stereospecific Suzuki-Miyaura Coupling of Chiral
 \a-(Acylamino)benzylboronic Esters with Inversion of Configuration
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13191
_journal_page_last               13193
_journal_paper_doi               10.1021/ja106632j
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_sum            'C22 H20 Cl N O2'
_chemical_formula_weight         365.84
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6619(3)
_cell_length_b                   10.3717(6)
_cell_length_c                   30.2873(14)
_cell_measurement_temperature    113(2)
_cell_volume                     1778.58(16)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            17126
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.8932
_exptl_absorpt_correction_T_min  0.8932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.214
_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   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0312P)^2^+0.7266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                3847
_reflns_number_total             4055
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja106632j_si_003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_Hall     p_2ac_2ab
_cod_database_code               4103135