Atom-economic and stereoselective catalytic synthesis of fully substituted enol esters/carbonates of amides in acyclic systems enabled by boron Lewis acid catalysis.
Xiao, Yuanjiu; Tang, Lei; Xu, Tong-Tong; Sheng, Jiang-Yi-Hui; Zhou, Zhongyan; Yue, Lei; Wang, Guoqiang; Oestreich, Martin; Feng, Jian-Jun; Chemical science 14 (2023) 5608–5618; doi:10.1039/d3sc01394d

data_1568970
_publ_section_title
;
 Atom-economic and stereoselective catalytic synthesis of fully
 substituted enol esters/carbonates of amides in acyclic systems enabled
 by boron Lewis acid catalysis.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              5608
_journal_page_last               5618
_journal_paper_doi               10.1039/d3sc01394d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C25 H26 Cl N O5'
_chemical_formula_sum            'C25 H26 Cl N O5'
_chemical_formula_weight         455.92
_chemical_name_systematic
'(E)-allyl (2-benzhydryl-5-chloro-1-(2-oxooxazolidin-3-yl)pent-1-en-1-yl) carbonate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-17 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.611(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5099(2)
_cell_length_b                   18.1304(3)
_cell_length_c                   14.0225(2)
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.5530
_cell_measurement_theta_min      4.8620
_cell_volume                     2328.55(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -33.00  32.00   1.00    1.00    --   34.48 -57.00  60.00   65
  2  \w     29.00  56.00   1.00    1.00    --   34.48 -99.00 -60.00   27
  3  \w     27.00  86.00   1.00    1.00    --   34.48-125.00-150.00   59
  4  \w     54.00 111.00   1.00    4.00    --  105.25-111.00-150.00   57
  5  \w     70.00 118.00   1.00    4.00    --  105.25 -45.00-120.00   48
  6  \w     52.00  96.00   1.00    4.00    --  105.25 -61.00-120.00   44
  7  \w     91.00 175.00   1.00    4.00    --  105.25  30.00  30.00   84
  8  \w    110.00 175.00   1.00    4.00    --  105.25 111.00  30.00   65
  9  \w    100.00 167.00   1.00    4.00    --  105.25 111.00-150.00   67
 10  \w    116.00 156.00   1.00    4.00    --  105.25 111.00-180.00   40
 11  \w     30.00 101.00   1.00    1.00    --   34.48  57.00-120.00   71
 12  \w     27.00  61.00   1.00    1.00    --   34.48  57.00-150.00   34
 13  \w     38.00 107.00   1.00    4.00    --  105.25 -94.00  30.00   69
 14  \w      5.00  61.00   1.00    1.00    --   34.48  19.00  90.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0126881000
_diffrn_orient_matrix_UB_12      0.0839310000
_diffrn_orient_matrix_UB_13      -0.0134252000
_diffrn_orient_matrix_UB_21      -0.0285210000
_diffrn_orient_matrix_UB_22      -0.0108569000
_diffrn_orient_matrix_UB_23      -0.1124502000
_diffrn_orient_matrix_UB_31      -0.1652640000
_diffrn_orient_matrix_UB_32      0.0083189000
_diffrn_orient_matrix_UB_33      -0.0127349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8080
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         4.082
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0438P)^2^+1.0283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3851
_reflns_number_total             4118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01394d2.cif
_cod_data_source_block           exp_2606
_cod_depositor_comments
'Adding full bibliography for 1568970--1568971.cif.'
_cod_database_code               1568970
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C20 H50 O5 N1 Cl1'
_shelx_estimated_absorpt_t_max   0.541
_shelx_estimated_absorpt_t_min   0.541
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00L(H00F,H00G), C00N(H00K,H00L), C00R(H00N,H00R), C00S(H00S,
 H00T), C00T(H00U,H00V)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00M(H00M),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00U(H00W), C00V(H00X)
;
_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 2.026
_oxdiff_exptl_absorpt_empirical_full_min 0.441