Catalytic asymmetric propargyl- and allylboration of hydrazonoesters: a metal-free approach to sterically encumbered chiral α-amino acid derivatives.
Jonker, Sybrand J. T.; Diner, Colin; Schulz, Göran; Iwamoto, Hiroaki; Eriksson, Lars; Szabó, Kálmán J; Chemical communications (Cambridge, England) 54 (2018) 12852–12855; doi:10.1039/c8cc07908k

data_7122506
_publ_section_title
;
 Catalytic asymmetric propargyl- and allylboration of hydrazonoesters: a
 metal-free approach to sterically encumbered chiral \a-amino acid
 derivatives.
;
_journal_issue                   91
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12852
_journal_page_last               12855
_journal_paper_doi               10.1039/c8cc07908k
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C56 H66 Br2 N4 O8'
_chemical_formula_sum            'C56 H66 Br2 N4 O8'
_chemical_formula_weight         1082.94
_chemical_melting_point          442
_chemical_name_systematic
'Ethyl (2S,3R)-2-(2-benzoyl-1-(4-bromobenzoyl)hydrazinyl)-3,7-dimethyl-3-vinyloct-6-enoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-06-20 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                100.702(3)
_cell_angle_beta                 99.312(4)
_cell_angle_gamma                92.569(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3142(5)
_cell_length_b                   10.6819(5)
_cell_length_c                   25.6534(13)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1
_cell_measurement_theta_min      12.2
_cell_volume                     2732.4(2)
_computing_cell_refinement       'APEX-3 (Bruker, 2017)'
_computing_data_collection       'APEX-3 (Bruker, 2017)'
_computing_data_reduction        'APEX-3 (Bruker, 2017)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      '77 (Liquid Nitrogen)'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 advance \k goniometer'
_diffrn_measurement_method       '\w scans and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2366
_diffrn_reflns_av_unetI/netI     0.1096
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            80613
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.518
_diffrn_reflns_theta_max         66.443
_diffrn_reflns_theta_min         3.556
_diffrn_source                   'Incotec 1myS Cu'
_exptl_absorpt_coefficient_mu    2.328
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5159
_exptl_absorpt_correction_type   multi-scan
_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            colour_less
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       stick
_exptl_crystal_F_000             1128
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol, water'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.00124(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         9649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+9.7270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6112
_reflns_number_total             9649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07908k2.cif
_cod_data_source_block           r
_cod_depositor_comments          'Adding full bibliography for 7122506.cif.'
_cod_database_code               7122506
_shelxl_version_number           2013-3
_shelx_res_checksum              26004