Synthesis of Chiral Tetrahydrofurans via Catalytic Asymmetric [3 + 2] Cycloaddition of Heterosubstituted Alkenes with Oxiranes.
Yuan, Xiao; Lin, Lili; Chen, Weiliang; Wu, Wangbin; Liu, Xiaohua; Feng, Xiaoming; The Journal of organic chemistry 81 (2016) 1237–1243; doi:10.1021/acs.joc.5b02524

data_4031823
_publ_section_title
;
 Synthesis of Chiral Tetrahydrofurans via Catalytic Asymmetric [3 + 2]
 Cycloaddition of Heterosubstituted Alkenes with Oxiranes.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1237
_journal_page_last               1243
_journal_paper_doi               10.1021/acs.joc.5b02524
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H22 O5'
_chemical_formula_sum            'C26 H22 O5'
_chemical_formula_weight         414.43
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   10.2142(4)
_cell_length_b                   10.2142(4)
_cell_length_c                   17.8299(7)
_cell_measurement_reflns_used    5823
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.6270
_cell_measurement_theta_min      4.9760
_cell_volume                     1610.97(11)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -32.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671  -77.0000 -180.0000 94

  2 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671   57.0000 -150.0000 84

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671  -99.0000    0.0000 74

  4 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671   57.0000  -60.0000 84

  5 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671 -125.0000    0.0000 66

  6 omega    6.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6671   19.0000   90.0000 101

  7 omega   91.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85

  8 omega   38.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

  9 omega   38.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 10 omega   40.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 95

 11 omega   38.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 12 omega   70.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 108

 13 omega   39.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 14 omega   38.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 15 omega   90.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

 16 omega   81.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 95

 17 omega   39.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -180.0000 125
;
_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      -0.1005333000
_diffrn_orient_matrix_UB_12      -0.0297784000
_diffrn_orient_matrix_UB_13      0.0695662000
_diffrn_orient_matrix_UB_21      -0.0483772000
_diffrn_orient_matrix_UB_22      -0.1689098000
_diffrn_orient_matrix_UB_23      -0.0033541000
_diffrn_orient_matrix_UB_31      0.1338526000
_diffrn_orient_matrix_UB_32      0.0298504000
_diffrn_orient_matrix_UB_33      0.0510910000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9751
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.992
_diffrn_reflns_theta_max         66.992
_diffrn_reflns_theta_min         5.000
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39317
_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    1.282
_exptl_crystal_description
;
;
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details
;
 Flack x determined using 1712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3833
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0738
_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^)+(0.1250P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3687
_reflns_number_total             3833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02524_si_002.cif
_cod_data_source_block           fxm-yx-1-2
_cod_depositor_comments          'Adding full bibliography for 4031823.cif.'
_cod_original_cell_volume        1610.98(13)
_cod_database_code               4031823
_reflns_odcompleteness_completeness 99.95
_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
2.a Ternary CH refined with riding coordinates:
 C006(H006), C00I(H00I), C00K(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00R(H00c,H00f), C00T(H00h,H00r)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G), C00J(H00J),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00S(H00S), C00U(H00U), C00V(H00V)
;
_shelx_res_checksum              64887
_shelx_hkl_checksum              69476
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-10
_olex2_submission_special_instructions 'No special instructions were received'