Chiral Allylic Amine Synthesis Enabled by the Enantioselective CpXRh(III)-Catalyzed Carboaminations of 1,3-Dienes
Wu, Liexin; Xu, Huiying; Gao, Hui; Li, Liping; Chen, Weijie; Zhou, Zhi; Yi, Wei; ACS Catalysis 11 (2021) 2279–2287; doi:10.1021/acscatal.0c04777

data_4518525
_publ_section_title
;
 Chiral Allylic Amine Synthesis Enabled by the Enantioselective
 CpXRh(III)-Catalyzed Carboaminations of 1,3-Dienes
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2279
_journal_page_last               2287
_journal_paper_doi               10.1021/acscatal.0c04777
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H27 N O2'
_chemical_formula_sum            'C22 H27 N O2'
_chemical_formula_weight         337.44
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0022(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.30461(16)
_cell_length_b                   7.07541(11)
_cell_length_c                   13.2130(2)
_cell_measurement_reflns_used    3743
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      72.5760
_cell_measurement_theta_min      4.2880
_cell_volume                     962.76(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -112.00 -16.00   1.00    2.00    --  -40.20 -38.00 120.00   96
  2  \w    -84.00  -6.00   1.00    2.00    --  -40.20 125.00 -60.00   78
  3  \w   -108.00 -16.00   1.00    2.00    --  -40.20 -38.00-150.00   92
  4  \w      7.00  63.00   1.00    2.00    --   40.20 -99.00  60.00   56
  5  \w    137.00 178.00   1.00    3.00    --  103.61  77.00 150.00   41
  6  \w     40.00 113.00   1.00    3.00    --  103.61-125.00 -30.00   73
  7  \w     28.00 136.00   1.00    3.00    --  103.61 -77.00 -30.00  108
  8  \w     30.00 113.00   1.00    3.00    --  103.61-125.00-180.00   83
  9  \w     68.00 134.00   1.00    3.00    --  103.61 -15.00-150.00   66
 10  \w     90.00 157.00   1.00    3.00    --  103.61  45.00  90.00   67
 11  \w     23.00 146.00   1.00    3.00    --  103.61 -15.00  90.00  123
 12  \w     23.00  49.00   1.00    3.00    --  103.61 -15.00-150.00   26
 13  \w     54.00 133.00   1.00    3.00    --  103.61 -61.00 120.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0299816000
_diffrn_orient_matrix_UB_12      0.0611022000
_diffrn_orient_matrix_UB_13      -0.1102436000
_diffrn_orient_matrix_UB_21      0.0436419000
_diffrn_orient_matrix_UB_22      -0.1954194000
_diffrn_orient_matrix_UB_23      -0.0373664000
_diffrn_orient_matrix_UB_31      -0.1399153000
_diffrn_orient_matrix_UB_32      -0.0741069000
_diffrn_orient_matrix_UB_33      0.0076281000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5915
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.522
_diffrn_reflns_theta_min         4.293
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(9)
_refine_ls_extinction_coef       0.0101(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0520P)^2^+0.1027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                3565
_reflns_number_total             3657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04777_si_002.cif
_cod_data_source_block           exp_4444
_cod_original_cell_volume        962.77(3)
_cod_database_code               4518525
_shelx_shelxl_version_number     2014/7
_diffrn_oxdiff_digest_frames
;
0130d7664ab7e3edd557300c890ed6cfa500028580c
;
_diffrn_oxdiff_digest_hkl
;
013d1863bbf8b2f395e18d7894cbf152cca8a6
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N9(H9), C5(H5), C16(H16), C25(H25), C21(H21), C3(H3), C15(H15), C24(H24),
 C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.492