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_7158557
_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         'C18 H28 N2 O6'
_chemical_formula_sum            'C18 H28 N2 O6'
_chemical_formula_weight         368.42
_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   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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.53431(4)
_cell_length_b                   11.74547(7)
_cell_length_c                   21.92815(13)
_cell_measurement_reflns_used    35554
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.1500
_cell_measurement_theta_min      3.7590
_cell_volume                     1940.510(19)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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     34.00  60.00   1.00    1.00    --    0.00  57.00  30.00   26
  2  \w    -15.00  40.00   1.00    1.00    --    0.00  37.00 150.00   55
  3  \w    -87.00 -17.00   1.00    1.00    --    0.00 -37.00  60.00   70
  4  \w    -22.00   9.00   1.00    1.00    --    0.00  57.00  30.00   31
  5  \w     56.00  81.00   1.00    1.00    --    0.00  77.00 -90.00   25
  6  \w     25.00  73.00   1.00    1.00    --    0.00  57.00-150.00   48
  7  \w    -25.00  22.00   1.00    1.00    --    0.00 -57.00  30.00   47
  8  \w     -8.00  19.00   1.00    1.00    --    0.00 -37.00  60.00   27
  9  \w    -30.00  50.00   1.00    1.00    --    0.00  77.00 -90.00   80
 10  \w    -86.00 -36.00   1.00    1.00    --    0.00 -37.00 -60.00   50
 11  \w     46.00  89.00   1.00    1.00    --    0.00  37.00 150.00   43
 12  \w    -88.00 -42.00   1.00    1.00    --    0.00 -57.00  30.00   46
 13  \w    -23.00  16.00   1.00    1.00    --    0.00  57.00-150.00   39
 14  \w    -80.00 -19.00   1.00    1.00    --    0.00 -37.00-120.00   61
 15  \w    -12.00  13.00   1.00    1.00    --    0.00 -37.00 -60.00   25
 16  \w     69.00  95.00   1.00    1.00    --   95.80  69.00 157.74   26
 17  \w     72.00 184.00   1.00    1.00    --   95.80  57.00 -74.47  112
 18  \w    156.00 182.00   1.00    1.00    --   95.80  58.00 -12.18   26
 19  \w    160.00 185.00   1.00    1.00    --   95.80  67.00 125.90   25
 20  \w     69.00 115.00   1.00    1.00    --   95.80  67.00 125.90   46
 21  \w     71.00  96.00   1.00    1.00    --   95.80  58.00 -12.18   25
 22  \w     72.00  98.00   1.00    1.00    --   95.80  56.00 -33.13   26
 23  \w     13.00 120.00   1.00    1.00    --   95.80 -61.00 -30.00  107
 24  \w     28.00 128.00   1.00    1.00    --   95.80 -82.00-180.00  100
 25  \w     75.00 132.00   1.00    1.00    --   95.80  45.00-120.00   57
 26  \w     72.00 106.00   1.00    1.00    --   95.80  61.00 150.00   34
 27  \w     61.00 128.00   1.00    1.00    --   95.80 -82.00-120.00   67
 28  \w     63.00  91.00   1.00    1.00    --   95.80  82.00  30.00   28
 29  \w     99.00 185.00   1.00    1.00    --   95.80  82.00  30.00   86
 30  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 31  \w     63.00  89.00   1.00    1.00    --   95.80  81.00 -89.34   26
 32  \w    139.00 165.00   1.00    1.00    --   95.80  74.00  24.14   26
 33  \w     71.00  98.00   1.00    1.00    --   95.80  61.00  79.04   27
 34  \w     66.00  92.00   1.00    1.00    --   95.80  74.00  24.14   26
 35  \w    113.00 173.00   1.00    1.00    --   95.80  82.00  81.85   60
 36  \w    123.00 184.00   1.00    1.00    --   95.80  75.00-123.68   61
 37  \w     73.00 184.00   1.00    1.00    --   95.80  60.00   5.44  111
 38  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 39  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 40  \w     71.00 140.00   1.00    1.00    --   95.80  61.00  30.00   69
 41  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 42  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 43  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 44  \w     71.00 123.00   1.00    1.00    --   95.80  61.00-120.00   52
 45  \w     66.00  92.00   1.00    1.00    --   95.80  77.00 120.00   26
 46  \w      6.00 125.00   1.00    1.00    --   95.80 -82.00  90.00  119
 47  \w     75.00 185.00   1.00    1.00    --   95.80  45.00 120.00  110
 48  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  81.85   25
 49  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 50  \w     76.00 169.00   1.00    1.00    --   95.80  45.00-180.00   93
 51  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -27.79   25
 52  \w     77.00 102.00   1.00    1.00    --   95.80  45.00  90.00   25
 53  \w     66.00  91.00   1.00    1.00    --   95.80  75.00-123.68   25
 54  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 55  \w     65.00  91.00   1.00    1.00    --   95.80  82.00  90.00   26
 56  \w     71.00  96.00   1.00    1.00    --   95.80  61.00-180.00   25
 57  \w     72.00 169.00   1.00    1.00    --   95.80  57.00-164.59   97
 58  \w     54.00  79.00   1.00    1.00    --   95.80 -82.00 120.00   25
 59  \w     87.00 112.00   1.00    1.00    --   95.80 -82.00 120.00   25
 60  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 61  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 62  \w     71.00 184.00   1.00    1.00    --   95.80  60.00 -51.17  113
 63  \w     65.00  90.00   1.00    1.00    --   95.80  76.00-160.46   25
 64  \w    126.00 151.00   1.00    1.00    --   95.80  56.00 -33.13   25
 65  \w    122.00 147.00   1.00    1.00    --   95.80  39.00  86.77   25
 66  \w     10.00 112.00   1.00    1.00    --   95.80 -82.00 -30.00  102
 67  \w     77.00 102.00   1.00    1.00    --   95.80  39.00  86.77   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      -0.1641494000
_diffrn_orient_matrix_UB_12      0.0622181000
_diffrn_orient_matrix_UB_13      -0.0253444000
_diffrn_orient_matrix_UB_21      0.0724586000
_diffrn_orient_matrix_UB_22      -0.0139660000
_diffrn_orient_matrix_UB_23      -0.0652424000
_diffrn_orient_matrix_UB_31      -0.0981398000
_diffrn_orient_matrix_UB_32      -0.1146312000
_diffrn_orient_matrix_UB_33      -0.0058186000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43698
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.270
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83516
_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    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0367P)^2^+0.3506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3427
_reflns_number_total             3438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00112h2.cif
_cod_data_source_block           exp_2459
_cod_original_cell_volume        1940.51(2)
_cod_database_code               7158557
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.810
_shelx_estimated_absorpt_t_min   0.734
_reflns_odcompleteness_completeness 99.95
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              82962
_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 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.816