Highly Enantioselective Construction of Fully Substituted Stereocenters Enabled by In Situ Phosphonium-Containing Organocatalysis
Zhang, Hongkui; Jiang, Chunhui; Tan, Jian-Ping; Hu, Hui-Lin; Chen, Yayun; Ren, Xiaoyu; Zhang, Hong-Su; Wang, Tianli; ACS Catalysis  (2020) 5698–5706; doi:10.1021/acscatal.0c01079

data_4517624
_publ_section_title
;
 Highly Enantioselective Construction of Fully Substituted Stereocenters
 Enabled by In Situ Phosphonium-Containing Organocatalysis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5698
_journal_page_last               5706
_journal_paper_doi               10.1021/acscatal.0c01079
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 N O5 S'
_chemical_formula_sum            'C19 H17 N O5 S'
_chemical_formula_weight         371.39
_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
_audit_creation_date             2019-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.712(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9914(2)
_cell_length_b                   19.2773(6)
_cell_length_c                   12.1358(3)
_cell_measurement_reflns_used    6519
_cell_measurement_temperature    292.8(4)
_cell_measurement_theta_max      72.4870
_cell_measurement_theta_min      4.2970
_cell_volume                     1869.41(9)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.8(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000   90.0000 66

  2 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000  -60.0000 88

  3 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  120.0000 88

  4 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000   30.0000 88

  5 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000 -150.0000 88

  6 omega   17.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -117.0000  -45.0000 68

  7 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000    0.0000 95

  8 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   60.0000 84

  9 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000  -30.0000 88

 10 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 11 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 12 omega   37.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -150.0000 109

 13 omega   41.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 85

 14 omega   38.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

 15 omega   38.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 78

 16 omega  100.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 78

 17 omega   38.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 18 omega   39.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 19 omega   38.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 20 omega   38.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

 21 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 22 omega   39.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0251968000
_diffrn_orient_matrix_UB_12      0.0065754000
_diffrn_orient_matrix_UB_13      -0.1257204000
_diffrn_orient_matrix_UB_21      -0.1384174000
_diffrn_orient_matrix_UB_22      -0.0557559000
_diffrn_orient_matrix_UB_23      0.0035260000
_diffrn_orient_matrix_UB_31      -0.1317755000
_diffrn_orient_matrix_UB_32      0.0568740000
_diffrn_orient_matrix_UB_33      0.0179149000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19543
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.575
_diffrn_reflns_theta_min         5.536
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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.
;
_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    1.320
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 2538 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6640
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0534
_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^)+(0.1063P)^2^+0.0539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.837
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                6337
_reflns_number_total             6640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01079_si_002.cif
_cod_data_source_block           wtl-wjh-1-2
_cod_depositor_comments          'Adding full bibliography for 4517624.cif.'
_cod_database_code               4517624
_reflns_odcompleteness_completeness 99.07
_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:
 C00G(H00G), C00Q(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C013(H01A,H01B), C01C(H01H,H01I)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00K(H00K), C00N(H00N), C00T(H00T), C00U(H00U), C00V(H00V),
 C00Z(H00Z), C011(H011), C012(H012), C014(H014), C016(H016), C017(H017),
 C018(H018), C01A(H01F), C01B(H01G), C01D(H01J)
2.d Idealised Me refined as rotating group:
 C00Y(H00A,H00B,H00C), C019(H01C,H01D,H01E), C01F(H01K,H01L,H01M), C01G(H01N,
 H01O,H01P)
;
_shelx_res_checksum              95940
_shelx_hkl_checksum              991
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-17
_olex2_submission_special_instructions 'No special instructions were received'