Diastereoselective arylation of bis-lactim ethers catalyzed by <i>N</i>-coordinating ylide-functionalized phosphine (NYPhos).
Sowa Prendes, Daniel; Löffler, Julian; Barreto, Ivan Martins; Sankaran, Nagesh; Remm, Henning; Nascimento de Oliveira, Ronaldo; Gessner, Viktoria H.; Gooßen, Lukas J; Chemical science 16 (2025) 14152–14160; doi:10.1039/d5sc02814k

data_1574992
_publ_section_title
;
 Diastereoselective arylation of bis-lactim ethers catalyzed by
 <i>N</i>-coordinating ylide-functionalized phosphine (NYPhos).
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              14152
_journal_page_last               14160
_journal_paper_doi               10.1039/d5sc02814k
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C37 H63 N3 P2'
_chemical_formula_sum            'C37 H63 N3 P2'
_chemical_formula_weight         611.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-16
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-03-18 deposited with the CCDC.	2025-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                102.6980(10)
_cell_angle_beta                 97.8380(10)
_cell_angle_gamma                114.7430(10)
_cell_formula_units_Z            4
_cell_length_a                   14.59100(10)
_cell_length_b                   17.3926(2)
_cell_length_c                   18.46600(10)
_cell_measurement_reflns_used    29799
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.6310
_cell_measurement_theta_min      2.5280
_cell_volume                     4011.60(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (G.M. Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     66.00 119.00   0.50    0.15    --   47.20  43.00 136.00  106
  2  \w     94.00 178.00   0.50    0.65    --  106.49  43.00 136.00  168
  3  \w    147.00 178.00   0.50    0.65    --  106.49  15.00 150.00   62
  4  \w     95.00 171.00   0.50    0.65    --  106.49  30.00  60.00  152
  5  \w     93.00 130.00   0.50    0.65    --  106.49  15.00 150.00   74
  6  \w    101.00 178.00   0.50    0.65    --  106.49  30.00  30.00  154
  7  \w     95.00 178.00   0.50    0.65    --  106.49  15.00 -60.00  166
  8  \w    102.00 131.00   0.50    0.65    --  106.49  77.00-180.00   58
  9  \w    146.00 171.00   0.50    0.65    --  106.49  77.00-180.00   50
 10  \w    -68.00  20.00   0.50    0.15    --  -47.20  77.00   0.00  176
 11  \w    -44.00  25.00   0.50    0.15    --  -47.20  43.00 136.00  138
 12  \w    -25.00  48.00   0.50    0.15    --   47.20 -43.00 -15.00  146
 13  \w    124.00 178.00   0.50    0.65    --  106.49 125.00 -30.00  108
 14  \w    -12.00  19.00   0.50    0.15    --  -47.20  19.00-120.00   62
 15  \w    -25.00   9.00   0.50    0.15    --   47.20 -19.00-120.00   68
 16  \w     34.00  97.00   0.50    0.65    --  106.49 -94.00 -30.00  126
 17  \w     34.00  95.00   0.50    0.15    --   47.20-125.00-180.00  122
 18  \w     45.00 125.00   0.50    0.65    --  106.49-144.00-108.37  160
 19  \w     77.00 106.00   0.50    0.65    --  106.49-101.00 -89.47   58
 20  \w     34.00  60.00   0.50    0.65    --  106.49-101.00 -89.47   52
 21  \w     34.00  99.00   0.50    0.65    --  106.49 -94.00 -90.00  130
 22  \w     99.00 127.00   0.50    0.65    --  106.49-146.00  74.13   56
 23  \w     53.00 113.00   0.50    0.65    --  106.49-136.00 116.69  120
 24  \w     41.00  89.00   0.50    0.65    --  106.49-125.00 150.00   96
 25  \w     45.00  84.00   0.50    0.65    --  106.49 -94.00 120.00   78
 26  \w     41.00  91.00   0.50    0.65    --  106.49 -94.00 150.00  100
 27  \w     34.00  62.00   0.50    0.65    --  106.49 -61.00 150.00   56
 28  \w     37.00  72.00   0.50    0.65    --  106.49 -61.00  60.00   70
 29  \w     36.00  76.00   0.50    0.65    --  106.49 -77.00  30.00   80
 30  \w     42.00  67.00   0.50    0.65    --  106.49 -61.00 120.00   50
 31  \w     37.00 108.00   0.50    0.65    --  106.49 -77.00 -30.00  142
 32  \w     44.00  82.00   0.50    0.65    --  106.49 -77.00 -90.00   76
 33  \w     43.00  68.00   0.50    0.65    --  106.49 -61.00 -90.00   50
 34  \w    -48.00 -19.00   0.50    0.65    --  -86.25  61.00 -60.00   58
 35  \w    -48.00 -15.00   0.50    0.65    --  -86.25  45.00 -90.00   66
 36  \w    -45.00 -20.00   0.50    0.65    --  -86.25  43.00 136.00   50
 37  \w   -101.00 -76.00   0.50    0.15    --  -47.20 -43.00 -15.00   50
 38  \w   -128.00 -79.00   0.50    0.65    --  -86.25 -43.00 -15.00   98
 39  \w   -119.00 -74.00   0.50    0.15    --  -47.20-125.00 -60.00   90
 40  \w   -119.00 -83.00   0.50    0.15    --  -47.20-125.00  60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1203112000
_diffrn_orient_matrix_UB_12      0.0466947000
_diffrn_orient_matrix_UB_13      0.0233063000
_diffrn_orient_matrix_UB_21      -0.0015119000
_diffrn_orient_matrix_UB_22      -0.0686947000
_diffrn_orient_matrix_UB_23      0.0407867000
_diffrn_orient_matrix_UB_31      -0.0000348000
_diffrn_orient_matrix_UB_32      -0.0600639000
_diffrn_orient_matrix_UB_33      -0.0750142000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            49997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         2.539
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.161
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.013
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.039
_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     759
_refine_ls_number_reflns         14305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0431P)^2^+1.4040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12885
_reflns_number_total             14305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02814k6.cif
_cod_data_source_block           JL-NK-23_a_sq
_cod_depositor_comments
'Adding full bibliography for 1574991--1574993.cif.'
_cod_original_cell_volume        4011.60(7)
_cod_database_code               1574992
_shelx_shelxl_version_number     2019/3
_cell_oxdiff_length_a            14.59104(14)
_cell_oxdiff_length_b            17.39262(17)
_cell_oxdiff_length_c            18.46604(13)
_cell_oxdiff_angle_alpha         102.6982(7)
_cell_oxdiff_angle_beta          97.8376(7)
_cell_oxdiff_angle_gamma         114.7425(9)
_cell_oxdiff_volume              4011.65(6)
_cell_oxdiff_measurement_reflns_used 29799
_oxdiff_exptl_absorpt_empirical_full_min 0.773
_oxdiff_exptl_absorpt_empirical_full_max 1.648
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         'C62 H61 N6 P4 O2'
_shelx_res_checksum              3881
_shelx_fab_checksum              64004