Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides.
Hu, Naifu; Zhao, Guoqing; Zhang, Yuanyuan; Liu, Xiangqian; Li, Guangyu; Tang, Wenjun; Journal of the American Chemical Society 137 (2015) 6746–6749; doi:10.1021/jacs.5b03760

data_4123693
_publ_section_title
;
 Synthesis of Chiral \a-Amino Tertiary Boronic Esters by Enantioselective
 Hydroboration of \a-Arylenamides.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6746
_journal_page_last               6749
_journal_paper_doi               10.1021/jacs.5b03760
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H33 O4 P Rh, B F4, H2 O'
_chemical_formula_sum            'C26 H35 B F4 O5 P Rh'
_chemical_formula_weight         648.23
_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'
_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_date             2014-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.643(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2826(9)
_cell_length_b                   8.1660(7)
_cell_length_c                   16.8783(15)
_cell_measurement_reflns_used    2623
_cell_measurement_temperature    130
_cell_measurement_theta_max      24.52
_cell_measurement_theta_min      2.51
_cell_volume                     1364.7(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13907
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.25
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0655 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.9137.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7947
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0235P)^2^+0.6659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                6441
_reflns_number_total             7947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b03760_si_001.cif
_cod_data_source_block           mo_dm14610_0m
_cod_depositor_comments
'Adding full bibliography for 4123693--4123694.cif.'
_cod_database_code               4123693
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Rotating group:
 O4(H4A,H4B)
2.c Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
2.d Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.e Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C21(H21),
 C22(H22), C23(H23)
2.f Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'