Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: synthesis of (+)-sappanone B.
Takikawa, Hiroshi; Suzuki, Keisuke; Organic letters 9 (2007) 2713–2716; doi:10.1021/ol070929p

data_1505433
_publ_section_title
;
 Modified chiral triazolium salts for enantioselective benzoin cyclization
 of enolizable keto-aldehydes: synthesis of (+)-sappanone B.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2713
_journal_page_last               2716
_journal_paper_doi               10.1021/ol070929p
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H24 O6'
_chemical_formula_sum            'C25 H24 O6'
_chemical_formula_weight         420.44
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1950(11)
_cell_length_b                   17.387(3)
_cell_length_c                   19.004(3)
_cell_measurement_reflns_used    2513
_cell_measurement_temperature    173(2)
_cell_volume                     2047.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1998)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART CCD area detector system'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1328
_diffrn_reflns_av_sigmaI/netI    0.1385
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19623
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.99
_diffrn_reflns_theta_min         1.59
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku Ultrax18'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'absorption was corrected by SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.841
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                2148
_reflns_number_total             4149
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070929psi20070420_023836.cif
_cod_data_source_block           irai06
_cod_database_code               1505433