Stereoselective synthesis of (E)-α,β-unsaturated esters: triethylamine-catalyzed allylic rearrangement of enol phosphates
Zhang, Yulong; Guo, Huichuang; Wu, Qian; Bi, Xiaojing; Shi, Enxue; Xiao, Junhua; RSC Advances 13 (2023) 13511–13515; doi:10.1039/D3RA02430J

data_7246780
_publ_section_title
;
 Stereoselective synthesis of (E)-\a,\b-unsaturated esters:
 triethylamine-catalyzed allylic rearrangement of enol phosphates
;
_journal_issue                   20
_journal_name_full               'RSC Advances'
_journal_page_first              13511
_journal_page_last               13515
_journal_paper_doi               10.1039/D3RA02430J
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C18 H19 O4 P'
_chemical_formula_sum            'C18 H19 O4 P'
_chemical_formula_weight         330.30
_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     direct
_audit_creation_date             2022-10-31
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-20 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                107.828(9)
_cell_angle_beta                 102.923(10)
_cell_angle_gamma                104.503(11)
_cell_formula_units_Z            2
_cell_length_a                   6.1976(8)
_cell_length_b                   12.1637(13)
_cell_length_c                   12.6520(13)
_cell_measurement_reflns_used    2939
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.2040
_cell_measurement_theta_min      3.8450
_cell_volume                     831.07(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    -41.00  31.00   1.00    1.00    --  -40.73  57.00  60.00   72
  2  \w    -69.00  31.00   1.00    1.00    --  -40.73  57.00-180.00  100
  3  \w     46.00  89.00   1.00    1.00    --   40.73-125.00   0.00   43
  4  \w     54.00 108.00   1.00    2.00    --  107.58 -94.00-120.00   54
  5  \w     38.00  77.00   1.00    2.00    --  107.58 -94.00-150.00   39
  6  \w     31.00 136.00   1.00    2.00    --  107.58 -30.00-180.00  105
  7  \w    127.00 175.00   1.00    2.00    --  107.58  45.00-150.00   48
  8  \w     83.00 138.00   1.00    2.00    --  107.58  30.00 120.00   55
  9  \w     84.00 174.00   1.00    2.00    --  107.58  61.00 150.00   90
 10  \w   -112.00 -45.00   1.00    1.00    --  -41.23 -77.00 -60.00   67
 11  \w   -119.00 -62.00   1.00    1.00    --  -41.23-162.00 153.00   57
 12  \w     24.00  64.00   1.00    1.00    --   41.23  38.00  30.00   40
 13  \w     77.00 116.00   1.00    1.00    --   41.23  38.00  30.00   39
 14  \w     40.00 122.00   1.00    2.00    --  106.95 -30.00  90.00   82
 15  \w    138.00 168.00   1.00    2.00    --  106.95 125.00  60.00   30
 16  \w     34.00 112.00   1.00    2.00    --  106.95-125.00  30.00   78
 17  \w     40.00 133.00   1.00    2.00    --  106.95 -61.00   0.00   93
 18  \w     56.00  94.00   1.00    2.00    --  106.95 -94.00 150.00   38
 19  \w     79.00 109.00   1.00    2.00    --  106.95 -94.00  60.00   30
 20  \w    132.00 158.00   1.00    2.00    --  106.95 117.00  30.00   26
 21  \w    115.00 141.00   1.00    2.00    --  106.95 125.00 150.00   26
 22  \w    132.00 158.00   1.00    2.00    --  106.95  61.00 -60.00   26
 23  \w    108.00 120.00   1.00    2.00    --  106.95 -45.00   0.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0988146000
_diffrn_orient_matrix_UB_12      0.0866526000
_diffrn_orient_matrix_UB_13      0.1305062000
_diffrn_orient_matrix_UB_21      0.1468945000
_diffrn_orient_matrix_UB_22      0.1006101000
_diffrn_orient_matrix_UB_23      -0.0308853000
_diffrn_orient_matrix_UB_31      -0.2058632000
_diffrn_orient_matrix_UB_32      0.0492279000
_diffrn_orient_matrix_UB_33      -0.0174519000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5688
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.882
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0931
_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^)+(0.1489P)^2^+1.0948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2526
_refine_ls_wR_factor_ref         0.2603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2353
_reflns_number_total             2912
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 139.3769\% 
 around [0.57 -0.33 -0.75] (reciprocal) or [0.94 -0.15 -0.30] (direct)
;
_cod_data_source_file            d3ra02430j2.cif
_cod_data_source_block           p4
_cod_original_cell_volume        831.07(18)
_cod_database_code               7246780
_shelx_shelxl_version_number     2017/1
_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:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              13496
_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 2.383
_oxdiff_exptl_absorpt_empirical_full_min 0.354
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2