An efficient [3+2] annulation for the asymmetric synthesis of densely-functionalized pyrrolidinones and γ-butenolides.
Qian, Hui; Sun, Song; Zhao, Wanxiang; Sun, Jianwei; Chemical communications (Cambridge, England) 56 (2020) 11295–11298; doi:10.1039/d0cc05188h

data_7127085
_publ_section_title
;
 An efficient [3+2] annulation for the asymmetric synthesis of
 densely-functionalized pyrrolidinones and \g-butenolides.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11295
_journal_page_last               11298
_journal_paper_doi               10.1039/d0cc05188h
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H31 N O4 S'
_chemical_formula_sum            'C28 H31 N O4 S'
_chemical_formula_weight         477.60
_chemical_name_systematic
(3S,4S,5R)-5-benzyl-3-butyl-4-hydroxy-4-phenyl-1-tosylpyrrolidin-2-one
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-05
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
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2015-02-05 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 117.558(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8701(4)
_cell_length_b                   9.35538(18)
_cell_length_c                   12.2790(4)
_cell_measurement_reflns_used    4315
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.4280
_cell_measurement_theta_min      6.2140
_cell_volume                     1208.87(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   80.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000   60.0000 98

  2 omega  -49.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6953   37.0000  -90.0000 84

  3 omega  -96.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6953  125.0000  -30.0000 94

  4 omega -115.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6953  -57.0000  120.0000 104

  5 omega  150.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  125.0000    0.0000 27

  6 omega   95.00  131.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  125.0000    0.0000 36

  7 omega   36.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -15.0000   30.0000 135

  8 omega   85.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000   60.0000 37

  9 omega   39.00  118.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  -30.0000 79

 10 omega   39.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000   60.0000 27

 11 omega   36.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  120.0000 72

 12 omega   36.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  120.0000 80

 13 omega   36.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -90.0000 52

 14 omega   31.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -90.0000 73
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1378860000
_diffrn_orient_matrix_UB_12      0.0472702000
_diffrn_orient_matrix_UB_13      0.0839438000
_diffrn_orient_matrix_UB_21      0.0326280000
_diffrn_orient_matrix_UB_22      -0.0221987000
_diffrn_orient_matrix_UB_23      -0.1065441000
_diffrn_orient_matrix_UB_31      -0.0366884000
_diffrn_orient_matrix_UB_32      0.1562311000
_diffrn_orient_matrix_UB_33      -0.0402011000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6698
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         4.20
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and diethyl ether'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.1831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0604
_reflns_number_gt                3310
_reflns_number_total             3391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc05188h2.cif
_cod_data_source_block           qian13cult
_cod_depositor_comments          'Adding full bibliography for 7127085.cif.'
_cod_original_cell_volume        1208.86(6)
_cod_database_code               7127085
_chemical_oxdiff_formula         'S1 O4 Ph6 N1'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C22(H22), C23(H23), C25(H25),
 C26(H26), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C34(H34A,H34B,H34C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_date_sample_data_collection 2015-02-03
_olex2_submission_special_instructions 'No special instructions were received'