Stereodivergent Asymmetric Synthesis of α,β-Disubstituted β-Aminoalkylboronic Acid Derivatives via Group-Selective Protodeboronation Enabling Access to the Elusive Anti Isomer.
Li, Xiangyu; Hall, Dennis G.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c03207

data_4134878
_publ_section_title
;
 Stereodivergent Asymmetric Synthesis of \a,\b-Disubstituted
 \b-Aminoalkylboronic Acid Derivatives via Group-Selective
 Protodeboronation Enabling Access to the Elusive Anti Isomer.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c03207
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C30 H32 B N O4'
_chemical_formula_sum            'C30 H32 B N O4'
_chemical_formula_weight         481.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 97.5578(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8361(2)
_cell_length_b                   21.0549(4)
_cell_length_c                   13.1959(2)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      73.49
_cell_measurement_theta_min      3.98
_cell_volume                     2709.10(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19724
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.249
_diffrn_reflns_theta_min         3.378
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8139
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 4486 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     764
_refine_ls_number_reflns         10891
_refine_ls_number_restraints     321
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1207P)^2^+0.4383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1760
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                10160
_reflns_number_total             10891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c03207_si_002.cif
_cod_data_source_block           dgh1917
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4134878
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.834
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              5171
_shelx_hkl_checksum              70602