Ni-catalyzed enantioselective three-component reductive alkylacylation of alkenes: modular access to structurally complex α-amino ketones.
Xiao, Jichao; Jia, Tingting; Chen, Shuang; Pan, Mengxiao; Li, Xingwei; Chemical science 15 (2024) 15489–15495; doi:10.1039/d4sc04561k

data_1572492
_publ_section_title
;
 Ni-catalyzed enantioselective three-component reductive alkylacylation of
 alkenes: modular access to structurally complex &#x3b1;-amino ketones.
;
_journal_issue                   37
_journal_name_full               'Chemical science'
_journal_page_first              15489
_journal_page_last               15495
_journal_paper_doi               10.1039/d4sc04561k
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N O2'
_chemical_formula_sum            'C20 H23 N O2'
_chemical_formula_weight         309.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-21 deposited with the CCDC.	2024-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.2015(5)
_cell_length_b                   18.4915(8)
_cell_length_c                   18.9255(9)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    242.00
_cell_measurement_theta_max      68.490
_cell_measurement_theta_min      3.341
_cell_volume                     3570.1(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      242.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            64173
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.808
_diffrn_reflns_theta_min         3.341
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1204 before and 0.0733 after correction.
The Ratio of minimum to maximum transmission is 0.8420.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 2702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         6483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0383P)^2^+0.5153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                6325
_reflns_number_total             6483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04561k2.cif
_cod_data_source_block           s
_cod_depositor_comments
'Adding full bibliography for 1572492--1572493.cif.'
_cod_database_code               1572492
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.845
_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 Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C22(H22), C24(H24), C28(H28), C30(H30), C36(H36), C40(H40), C5(H5),
 C21(H21), C11(H11), C23(H23), C13(H13), C29(H29), C15(H15), C31(H31), C2(H2),
 C33(H33), C37(H37), C19(H19), C39(H39)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C7(H7A,H7B,H7C), C17(H17A,H17B,
 H17C), C35(H35A,H35B,H35C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              14110
_olex2_submission_special_instructions 'No special instructions were received'