Palladium-catalyzed asymmetric sequential hydroalkylation and hydroamination of 1,3-enynes with 3-hydroxyindoles
Li, Qiuyu; Wu, Ruixue; Wu, Tianbao; Wei, Renkang; Li, Zhijiao; Gao, Shang; Wang, Minyan; Yao, Hequan; Lin, Aijun; Green Chemistry 28 (2026) 3232–3242; doi:10.1039/D5GC05558J

data_7251608
_publ_section_title
;
 Palladium-catalyzed asymmetric sequential hydroalkylation and
 hydroamination of 1,3-enynes with 3-hydroxyindoles
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              3232
_journal_page_last               3242
_journal_paper_doi               10.1039/D5GC05558J
_journal_volume                  28
_journal_year                    2026
_chemical_formula_sum            'C38 H40 N2 O5'
_chemical_formula_weight         604.72
_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   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-07-16 deposited with the CCDC.	2026-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.234(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.3057(4)
_cell_length_b                   6.32680(10)
_cell_length_c                   16.4984(4)
_cell_measurement_temperature    170(2)
_cell_volume                     1597.27(6)
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32890
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.691
_diffrn_reflns_theta_min         2.679
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5449
_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_density_diffrn    1.257
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(13)
_refine_ls_extinction_coef       0.0044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6435
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+0.3862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                5877
_reflns_number_total             6435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc05558j2.cif
_cod_data_source_block           cu_20232069_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7251608
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.907
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              63058
_shelx_hkl_checksum              48405