Highly enantioselective oxazaborolidine-catalyzed reduction of 1,3-dicarbonyl compounds: role of the additive diethylaniline.
Chein, Rong-Jie; Yeung, Ying-Yeung; Corey, E. J.; Organic letters 11 (2009) 1611–1614; doi:10.1021/ol900258f

data_1503836
_publ_section_title
;
 Highly enantioselective oxazaborolidine-catalyzed reduction of
 1,3-dicarbonyl compounds: role of the additive diethylaniline.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1611
_journal_page_last               1614
_journal_paper_doi               10.1021/ol900258f
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C26 H24 Br2 O2'
_chemical_formula_moiety         'C26 H24 Br2 O2'
_chemical_formula_structural     'C26 H24 Br2 O2'
_chemical_formula_sum            'C26 H24 Br2 O2'
_chemical_formula_weight         528.27
_chemical_name_common            RJ-001-X
_chemical_name_systematic
; 
(<i>R</i>)-2,2-Dibenzylcyclopentyl 3,5-dibromobenzoate
;
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      144
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   13.4765(1)
_cell_length_b                   13.4765(1)
_cell_length_c                   10.5602(2)
_cell_measurement_reflns_used    8247
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.60
_cell_volume                     1660.95(4)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1840 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31763
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.681
_exptl_absorpt_correction_T_max  0.8374
_exptl_absorpt_correction_T_min  0.4597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             798
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         6430
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0166P)^2^+0.0375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                5176
_reflns_number_total             6430
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol900258f_si_002.cif
_cod_data_source_block           ejc151
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1503836