Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable Diastereoselectivity.
Nechaev, Anton A.; Van Hecke, Kristof; Zaman, Manzoor; Kashtanov, Stepan; Ungur, Liviu; Pereshivko, Olga P.; Peshkov, Vsevolod A.; Van der Eycken, Erik V.; The Journal of organic chemistry 83 (2018) 8170–8182; doi:10.1021/acs.joc.8b00953

data_4035574
_publ_section_title
;
 Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable
 Diastereoselectivity.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8170
_journal_page_last               8182
_journal_paper_doi               10.1021/acs.joc.8b00953
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C22 H24 N2 O3'
_chemical_formula_sum            'C22 H24 N2 O3'
_chemical_formula_weight         364.43
_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   mixed
_audit_creation_date             2017-09-18
_audit_creation_method
;
Olex2 1.2
(compiled Aug 10 2017 17:28:52 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                65.187(2)
_cell_angle_beta                 85.6988(15)
_cell_angle_gamma                89.9095(15)
_cell_formula_units_Z            4
_cell_length_a                   10.06464(15)
_cell_length_b                   13.9350(3)
_cell_length_c                   16.1031(3)
_cell_measurement_reflns_used    46512
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.2620
_cell_measurement_theta_min      4.3670
_cell_volume                     2043.09(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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   -114.00 -14.00   1.00    2.00    --  -41.68 -55.00  36.00  100
  2  \w    -69.00  30.00   1.00    2.00    --  -41.68  55.00 179.00   99
  3  \w     14.00 114.00   1.00    2.00    --   41.68  55.00 179.00  100
  4  \w     37.00 137.00   1.00    8.00    --  109.13 -55.00  36.00  100
  5  \w     81.00 178.00   1.00    8.00    --  109.13  55.00 179.00   97
  6  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 -90.00  101
  7  \w      1.00  83.00   1.00    2.00    --   41.68 -99.00   0.00   82
  8  \w     23.00  98.00   1.00    2.00    --   41.68-125.00 -90.00   75
  9  \w    -30.00  69.00   1.00    2.00    --   41.68 -55.00  36.00   99
 10  \w     17.00 116.00   1.00    2.00    --   41.68  38.00 -60.00   99
 11  \w     26.00 109.00   1.00    8.00    --  109.13 -94.00 120.00   83
 12  \w     80.00 178.00   1.00    8.00    --  109.13  61.00 -30.00   98
 13  \w     36.00 121.00   1.00    8.00    --  109.13-125.00  60.00   85
 14  \w     79.00 178.00   1.00    8.00    --  109.13  67.00-132.88   99
 15  \w     81.00 178.00   1.00    8.00    --  109.13  30.00 -30.00   97
 16  \w     80.00 178.00   1.00    8.00    --  109.13  61.00 -90.00   98
 17  \w     26.00 109.00   1.00    8.00    --  109.13 -94.00-120.00   83
 18  \w     77.00 178.00   1.00    8.00    --  109.13  77.00 -90.00  101
 19  \w     83.00 178.00   1.00    8.00    --  109.13  45.00 -90.00   95
 20  \w     82.00 178.00   1.00    8.00    --  109.13  50.00 -41.64   96
 21  \w     80.00 178.00   1.00    8.00    --  109.13  61.00 -60.00   98
 22  \w     77.00 178.00   1.00    8.00    --  109.13  77.00  60.00  101
 23  \w     80.00 178.00   1.00    8.00    --  109.13  61.00-120.00   98
 24  \w     77.00 178.00   1.00    8.00    --  109.13  73.00 -95.29  101
 25  \w     83.00 178.00   1.00    8.00    --  109.13  45.00 -30.00   95
 26  \w     94.00 178.00   1.00    8.00    --  109.13 125.00  90.00   84
 27  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00-120.00  109
 28  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00 150.00  109
 29  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00  30.00  109
 30  \w   -122.00  -1.00   1.00    2.00    --  -41.68 -19.00  60.00  121
 31  \w      1.00  83.00   1.00    2.00    --   41.68 -99.00 -90.00   82
 32  \w     17.00 116.00   1.00    2.00    --   41.68  38.00-150.00   99
 33  \w      9.00 118.00   1.00    2.00    --   41.68  77.00  30.00  109
 34  \w      9.00 118.00   1.00    2.00    --   41.68  77.00 150.00  109
 35  \w     77.00 178.00   1.00    8.00    --  109.13  77.00 -30.00  101
 36  \w     80.00 178.00   1.00    8.00    --  109.13  61.00-180.00   98
 37  \w     80.00 178.00   1.00    8.00    --  109.13  61.00 150.00   98
 38  \w     77.00 178.00   1.00    8.00    --  109.13  77.00  30.00  101
 39  \w     77.00 178.00   1.00    8.00    --  109.13  77.00-180.00  101
 40  \w     80.00 178.00   1.00    8.00    --  109.13  61.00  90.00   98
 41  \w     80.00 178.00   1.00    8.00    --  109.13  61.00   0.00   98
 42  \w     80.00 178.00   1.00    8.00    --  109.13  61.00 120.00   98
 43  \w     80.00 178.00   1.00    8.00    --  109.13  61.00  60.00   98
 44  \w     26.00 109.00   1.00    8.00    --  109.13 -94.00-180.00   83
 45  \w     83.00 178.00   1.00    8.00    --  109.13  45.00  30.00   95
 46  \w     77.00 178.00   1.00    8.00    --  109.13  77.00  90.00  101
 47  \w     77.00 178.00   1.00    8.00    --  109.13  77.00 120.00  101
 48  \w     82.00 178.00   1.00    8.00    --  109.13  52.00-125.40   96
 49  \w     80.00 178.00   1.00    8.00    --  109.13  61.00  30.00   98
 50  \w     80.00 178.00   1.00    8.00    --  109.13  61.00-150.00   98
 51  \w   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00-180.00   99
 52  \w   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00-120.00   99
 53  \w   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00 150.00   99
 54  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00   0.00  101
 55  \w    -46.00 130.00   1.00    2.00    --   41.68   0.00-180.00  176
 56  \w     14.00 115.00   1.00    2.00    --   41.68  57.00-120.00  101
 57  \w    -46.00 130.00   1.00    2.00    --   41.68   0.00-150.00  176
 58  \w      9.00 118.00   1.00    2.00    --   41.68  77.00 -90.00  109
 59  \w     26.00  97.00   1.00    8.00    --  109.13 -94.00  30.00   71
 60  \w     81.00 178.00   1.00    8.00    --  109.13  57.00  74.61   97
 61  \w     77.00 178.00   1.00    8.00    --  109.13  77.00   0.00  101
 62  \w     77.00 178.00   1.00    8.00    --  109.13  77.00-120.00  101
 63  \w     77.00 178.00   1.00    8.00    --  109.13  77.00 -60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0294845000
_diffrn_orient_matrix_UB_12      -0.0715846000
_diffrn_orient_matrix_UB_13      0.1030432000
_diffrn_orient_matrix_UB_21      -0.1199800000
_diffrn_orient_matrix_UB_22      0.0672744000
_diffrn_orient_matrix_UB_23      0.0037052000
_diffrn_orient_matrix_UB_31      -0.0912217000
_diffrn_orient_matrix_UB_32      -0.0721648000
_diffrn_orient_matrix_UB_33      -0.0235314000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            78067
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.711
_diffrn_reflns_theta_min         3.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         8339
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0514P)^2^+0.7997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7706
_reflns_number_total             8339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00953_si_002.cif
_cod_data_source_block           evde_ugent009_sq
_cod_database_code               4035574
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C22 H24 N2 O3'
_reflns_odcompleteness_completeness 99.97
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2 = N4-H4
 0.88 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C11(H11), C33(H33)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31), C35(H35),
  C36(H36), C37(H37), C38(H38), C39(H39)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C27(H27A,H27B,H27C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,
 H44B,H44C)
;
_shelx_res_checksum              43249
_shelx_hkl_checksum              87283
_shelx_fab_checksum              10582
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 1.226
_oxdiff_exptl_absorpt_empirical_full_min 0.847