Asymmetric Construction of Tertiary/Secondary Carbon–Phosphorus Bonds via Bifunctional Phosphonium Salt Catalyzed 1,6-Addition
Chen, Yuan; Yu, Zhaoyuan; Jiang, Zhiyu; Tan, Jian-Ping; Wu, Jia-Hong; Lan, Yu; Ren, Xiaoyu; Wang, Tianli; ACS Catalysis 11 (2021) 14168–14180; doi:10.1021/acscatal.1c03149

data_4519161
_publ_section_title
;
 Asymmetric Construction of Tertiary/Secondary Carbon--Phosphorus Bonds
 via Bifunctional Phosphonium Salt Catalyzed 1,6-Addition
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              14168
_journal_page_last               14180
_journal_paper_doi               10.1021/acscatal.1c03149
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'I, C28 H42 N2 O3 P'
_chemical_formula_sum            'C28 H42 I N2 O3 P'
_chemical_formula_weight         612.50
_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             2019-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.069(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2419(3)
_cell_length_b                   15.1653(5)
_cell_length_c                   10.3309(3)
_cell_measurement_reflns_used    6499
_cell_measurement_temperature    294.3(8)
_cell_measurement_theta_max      72.5090
_cell_measurement_theta_min      5.2700
_cell_volume                     1563.05(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
;
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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.3(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega   18.00  106.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000  150.0000 88

  2 omega  -32.00   18.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000   90.0000 50

  3 omega   13.00   61.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -150.0000 48

  4 omega   20.00   46.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -180.0000 26

  5 omega    1.00   71.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -180.0000 70

  6 omega   19.00   45.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000    0.0000 26

  7 omega   29.00   74.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000   90.0000 45

  8 omega   47.00   73.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -180.0000 26

  9 omega   21.00   47.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000   90.0000 26

 10 omega   32.00   66.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000    0.0000 34

 11 omega   14.00   53.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   19.0000  -30.0000 39

 12 omega   10.00   44.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  150.0000 34

 13 omega   13.00   92.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   19.0000 -120.0000 79

 14 omega   11.00   76.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -120.0000 65

 15 omega  -31.00   54.00   1.0000    2.6200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000 -120.0000 85

 16 omega   91.00  116.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 25

 17 omega   81.00  107.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 18 omega   92.00  127.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 35

 19 omega  136.00  162.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 26

 20 omega   92.00  118.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 26

 21 omega   95.00  121.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 26

 22 omega   81.00  107.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 26

 23 omega   90.00  122.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 32

 24 omega   90.00  116.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 26

 25 omega   89.00  124.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 35

 26 omega   89.00  115.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 26

 27 omega   90.00  174.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 84

 28 omega  110.00  166.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 56

 29 omega   81.00  107.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 30 omega   88.00  119.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 31

 31 omega   81.00  107.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

 32 omega   40.00   98.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 33 omega   88.00  134.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 46

 34 omega  133.00  159.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 26

 35 omega  120.00  176.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 56

 36 omega   81.00  107.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

 37 omega   90.00  171.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 81

 38 omega   91.00  125.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 34

 39 omega   93.00  119.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 26

 40 omega   91.00  117.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 26

 41 omega   84.00  110.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 42 omega   40.00  108.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 68

 43 omega   81.00  107.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

 44 omega   90.00  116.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 26

 45 omega   91.00  117.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 26

 46 omega   84.00  110.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 26

 47 omega   38.00   64.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 26

 48 omega  151.00  176.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 25

 49 omega   99.00  150.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 51

 50 omega   81.00  107.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 51 omega   40.00   81.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 41

 52 omega  143.00  169.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000 -172.6390 26

 53 omega   84.00  110.00   1.0000   10.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000 -172.6390 26
;
_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      0.0713130000
_diffrn_orient_matrix_UB_12      0.0091286000
_diffrn_orient_matrix_UB_13      0.1475593000
_diffrn_orient_matrix_UB_21      -0.1368617000
_diffrn_orient_matrix_UB_22      0.0011429000
_diffrn_orient_matrix_UB_23      0.0383581000
_diffrn_orient_matrix_UB_31      0.0048849000
_diffrn_orient_matrix_UB_32      -0.1011779000
_diffrn_orient_matrix_UB_33      0.0136952000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15747
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.810
_diffrn_reflns_theta_min         4.394
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23795
_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    1.301
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.192
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details
;
 Flack x determined using 1895 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5421
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0643
_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^)+(0.1304P)^2^+0.0263P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1704
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.769
_reflns_Friedel_fraction_max     0.743
_reflns_number_gt                5120
_reflns_number_total             5421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03149_si_002.cif
_cod_data_source_block           wtl-wth-l.l
_cod_database_code               4519161
_reflns_odcompleteness_completeness 99.79
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C41(H41), C13(H13), C9(H9), C2BA(H2BA)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N0AA(H0AA), N6AA(H6AA), C9AA(H9AA), C5AA(H5AA), C6AA(H6AB), C7AA(H7AA),
 C8AA(H8AA), C16(H16), C19(H19), C6(H6), C0BA(H0BA), C0AA(H0AB)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C),
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C4AA(H4AA,H4AB,H4AC)
;
_shelx_res_checksum              98108
_shelx_hkl_checksum              19883
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-03-13
_olex2_submission_special_instructions 'No special instructions were received'