Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Catalyzed by Rare-Earth Amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 with Phenoxy-Functionalized Chiral Prolinols.
Zeng, Chao; Yuan, Dan; Zhao, Bei; Yao, Yingming; Organic letters 17 (2015) 2242–2245; doi:10.1021/acs.orglett.5b00833

data_1520304
_publ_section_title
;
 Highly Enantioselective Epoxidation of \a,\b-Unsaturated Ketones
 Catalyzed by Rare-Earth Amides [(Me3Si)2N]3RE(\m-Cl)Li(THF)3 with
 Phenoxy-Functionalized Chiral Prolinols.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2242
_journal_page_last               2245
_journal_paper_doi               10.1021/acs.orglett.5b00833
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         '(C64 H79 N2 O4 Yb), 0.333(C7 H8)'
_chemical_formula_sum            'C66.33 H81.67 N2 O4 Yb'
_chemical_formula_weight         1144.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   15.5920(6)
_cell_length_b                   20.5827(3)
_cell_length_c                   60.0650(12)
_cell_measurement_reflns_used    15879
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      72.49
_cell_measurement_theta_min      3.10
_cell_volume                     19276.4(9)
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_sigmaI/netI    0.1067
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       74
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            146419
_diffrn_reflns_theta_full        73.77
_diffrn_reflns_theta_max         73.77
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    3.024
_exptl_absorpt_correction_T_max  0.7725
_exptl_absorpt_correction_T_min  0.5692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.32
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             7148
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_platon_squeeze_details
;
;
_refine_diff_density_max         2.335
_refine_diff_density_min         -1.111
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.035(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1969
_refine_ls_number_reflns         38442
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0710
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1855
_reflns_number_gt                27397
_reflns_number_total             38442
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol5b00833_si_001.cif
_cod_data_source_block           g
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
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_cod_database_code               1520304