Enantioselective direct vinylogous Michael addition for constructing enantioenriched γ,γ-dialkyl substituted butyrolactams and octahydroindoles
Yan, Jiahang; Zhang, Wenting; He, Qiaoqiao; Hou, Jun; Zeng, Hongxin; Wei, Hongbo; Xie, Weiqing; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00112H

data_7158558
_publ_section_title
;
 Enantioselective direct vinylogous Michael addition for constructing
 enantioenriched \g,\g-dialkyl substituted butyrolactams and
 octahydroindoles
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00112H
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H24 Cl N O4'
_chemical_formula_sum            'C20 H24 Cl N O4'
_chemical_formula_weight         377.85
_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     dual
_audit_creation_date             2021-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-18 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.41290(10)
_cell_length_b                   6.44320(10)
_cell_length_c                   24.3361(3)
_cell_measurement_reflns_used    22661
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.0840
_cell_measurement_theta_min      3.6780
_cell_volume                     1909.70(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -29.00  23.00   1.00    1.00    --    0.00 -57.00   4.00   52
  2  \w     -8.00  30.00   1.00    1.00    --    0.00  57.00 146.00   38
  3  \w     72.00 101.00   1.00    1.00    --   95.80  57.00 146.00   29
  4  \w     22.00 104.00   1.00    1.00    --   95.80 -57.00   4.00   82
  5  \w     46.00  87.00   1.00    1.00    --    0.00  57.00-120.00   41
  6  \w    -18.00  24.00   1.00    1.00    --    0.00 -19.00  60.00   42
  7  \w     38.00  72.00   1.00    1.00    --    0.00  37.00  30.00   34
  8  \w     17.00  89.00   1.00    1.00    --    0.00  37.00-180.00   72
  9  \w    -23.00  40.00   1.00    1.00    --    0.00  57.00-120.00   63
 10  \w    -22.00  17.00   1.00    1.00    --    0.00  19.00 150.00   39
 11  \w    -83.00  12.00   1.00    1.00    --    0.00 -37.00-180.00   95
 12  \w    -10.00  25.00   1.00    1.00    --    0.00  37.00  30.00   35
 13  \w     59.00  85.00   1.00    1.00    --    0.00  19.00 150.00   26
 14  \w    -30.00  54.00   1.00    1.00    --    0.00  77.00 -30.00   84
 15  \w    -88.00 -29.00   1.00    1.00    --    0.00 -19.00  60.00   59
 16  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 17  \w     75.00 104.00   1.00    1.00    --   95.80  45.00 120.00   29
 18  \w     65.00  93.00   1.00    1.00    --   95.80  77.00-120.00   28
 19  \w     60.00 128.00   1.00    1.00    --   95.80 -82.00   0.00   68
 20  \w    104.00 130.00   1.00    1.00    --   95.80  45.00-120.00   26
 21  \w     68.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   60
 22  \w     63.00 122.00   1.00    1.00    --   95.80  82.00  60.00   59
 23  \w    150.00 182.00   1.00    1.00    --   95.80  82.00 150.00   32
 24  \w     75.00 100.00   1.00    1.00    --   95.80  45.00-120.00   25
 25  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 26  \w     63.00  98.00   1.00    1.00    --   95.80  82.00-150.00   35
 27  \w    105.00 184.00   1.00    1.00    --   95.80  82.00-150.00   79
 28  \w     71.00 183.00   1.00    1.00    --   95.80  61.00  30.00  112
 29  \w     73.00  99.00   1.00    1.00    --   95.80  61.00 -60.00   26
 30  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 31  \w     75.00 185.00   1.00    1.00    --   95.80  45.00 -60.00  110
 32  \w     70.00  95.00   1.00    1.00    --   95.80  62.00-137.57   25
 33  \w    140.00 181.00   1.00    1.00    --   95.80  62.00-137.57   41
 34  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 35  \w      6.00 127.00   1.00    1.00    --   95.80 -82.00 150.00  121
 36  \w    126.00 152.00   1.00    1.00    --   95.80  77.00 -60.00   26
 37  \w     34.00  59.00   1.00    1.00    --   95.80 -82.00-150.00   25
 38  \w     75.00 165.00   1.00    1.00    --   95.80  45.00 -90.00   90
 39  \w    132.00 177.00   1.00    1.00    --   95.80  79.00  45.99   45
 40  \w     75.00 156.00   1.00    1.00    --   95.80  45.00-180.00   81
 41  \w     63.00  96.00   1.00    1.00    --   95.80  82.00-180.00   33
 42  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 43  \w     77.00 103.00   1.00    1.00    --   95.80  45.00 150.00   26
 44  \w    134.00 178.00   1.00    1.00    --   95.80  45.00 150.00   44
 45  \w     69.00  95.00   1.00    1.00    --   95.80  79.00  45.99   26
 46  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 47  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 48  \w     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 49  \w     65.00  92.00   1.00    1.00    --   95.80  77.00  90.00   27
 50  \w    111.00 183.00   1.00    1.00    --   95.80  77.00  90.00   72
 51  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 52  \w     83.00 115.00   1.00    1.00    --   95.80 -82.00 -60.00   32
 53  \w     43.00  79.00   1.00    1.00    --   95.80 -82.00 -60.00   36
 54  \w     74.00 184.00   1.00    1.00    --   95.80  51.00  58.33  110
 55  \w     71.00 175.00   1.00    1.00    --   95.80  61.00   0.00  104
 56  \w     70.00  96.00   1.00    1.00    --   95.80  64.00-174.64   26
 57  \w    126.00 151.00   1.00    1.00    --   95.80  77.00-180.00   25
 58  \w     70.00  96.00   1.00    1.00    --   95.80  62.00 121.44   26
 59  \w    159.00 184.00   1.00    1.00    --   95.80  62.00 121.44   25
 60  \w    148.00 184.00   1.00    1.00    --   95.80  52.00 -25.40   36
 61  \w     73.00  99.00   1.00    1.00    --   95.80  52.00 -25.40   26
 62  \w     74.00 100.00   1.00    1.00    --   95.80  61.00  60.00   26
 63  \w     68.00  94.00   1.00    1.00    --   95.80  70.00 -26.29   26
 64  \w     88.00 113.00   1.00    1.00    --   95.80 -82.00  60.00   25
 65  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 66  \w    125.00 164.00   1.00    1.00    --   95.80  45.00 120.00   39
 67  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 68  \w    148.00 173.00   1.00    1.00    --   95.80  75.00  -4.79   25
 69  \w     67.00  92.00   1.00    1.00    --   95.80  75.00  -4.79   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0836107000
_diffrn_orient_matrix_UB_12      0.1638191000
_diffrn_orient_matrix_UB_13      0.0111638000
_diffrn_orient_matrix_UB_21      0.0906574000
_diffrn_orient_matrix_UB_22      0.1088486000
_diffrn_orient_matrix_UB_23      0.0423496000
_diffrn_orient_matrix_UB_31      0.0281004000
_diffrn_orient_matrix_UB_32      0.1359916000
_diffrn_orient_matrix_UB_33      -0.0473700000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            42350
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         3.629
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2812 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(5)
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         6817
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0513P)^2^+0.1130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6431
_reflns_number_total             6817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00112h2.cif
_cod_data_source_block           exp_2460
_cod_database_code               7158558
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.670
_shelx_estimated_absorpt_t_min   0.536
_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.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C25(H25), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C22(H22A,H22B), C23(H23A,H23B),
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C35(H35), C36(H36), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,
 H20C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,
 H40B,H40C)
;
_shelx_res_checksum              83161
_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.566