Pd(II)-catalyzed regioselective hydroarylation of allenyl-containing α-amino acid derivatives with aryl boronic acids.
Bubnova, Alexandra S.; Philippova, Anna N.; Gribanov, Pavel S.; Smol'yakov, Alexander F.; Osipov, Sergey N.; Vorobyeva, Daria V.; Organic & biomolecular chemistry 23 (2025) 5396–5400; doi:10.1039/d5ob00622h

data_7160527
_publ_section_title
;
 Pd(II)-catalyzed regioselective hydroarylation of allenyl-containing
 &#x3b1;-amino acid derivatives with aryl boronic acids.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5396
_journal_page_last               5400
_journal_paper_doi               10.1039/d5ob00622h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C30 H32 N2 O4'
_chemical_formula_sum            'C30 H32 N2 O4'
_chemical_formula_weight         484.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-10
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-04-10 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                70.51(3)
_cell_angle_beta                 74.23(3)
_cell_angle_gamma                85.57(4)
_cell_formula_units_Z            2
_cell_length_a                   9.531(10)
_cell_length_b                   11.853(14)
_cell_length_c                   12.147(14)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    120
_cell_measurement_theta_max      20.28
_cell_measurement_theta_min      2.49
_cell_volume                     1245(2)
_computing_cell_refinement       'SAINT V8.30A (22 Oct 2012)'
_computing_data_reduction        'SAINT V8.30A (22 Oct 2012)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1473
_diffrn_reflns_av_unetI/netI     0.3111
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10579
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.843
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1230 before and 0.0867 after correction.
The Ratio of minimum to maximum transmission is 0.5422.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.857
_refine_ls_R_factor_all          0.2045
_refine_ls_R_factor_gt           0.0976
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1961
_reflns_number_total             4820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00622h2.cif
_cod_data_source_block           bas_175
_cod_depositor_comments          'Adding full bibliography for 7160527.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7160527
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.976
_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
2.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C32(H32B,H32A,H32C), C33(H33A,H33B,
 H33C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              50967
_olex2_submission_special_instructions 'No special instructions were received'