Primary Alkylboronic Acids as Highly Active Catalysts for the Dehydrative Amide Condensation of α-Hydroxycarboxylic Acids
Yamashita, Risa; Sakakura, Akira; Ishihara, Kazuaki; Organic Letters 15 (2013) 3654–; doi:10.1021/ol401537f

data_1512187
_publ_section_title
;
 Primary Alkylboronic Acids as Highly Active Catalysts for the Dehydrative
 Amide Condensation of \a-Hydroxycarboxylic Acids
;
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              3654
_journal_paper_doi               10.1021/ol401537f
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C20 H24 B N O3'
_chemical_formula_weight         337.21
_chemical_name_systematic
; 
Tetrahydroquinolin-1-ium 4-benzylidene-2-hydroxy-2-methyl-5-oxo-1,3,2-dioxaborolan-2-uide 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.110(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.757(2)
_cell_length_b                   8.4756(17)
_cell_length_c                   19.340(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1758.7(6)
_computing_cell_refinement       'Bruker SMART'
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12186
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0608
_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/[?^2^(Fo^2^)+(0.1321P)^2^+0.9019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.1993
_reflns_number_gt                3630
_reflns_number_total             4363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401537f_si_002.cif
_cod_data_source_block           ryf1
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1512187