Secondary stereocontrolling interactions in chiral Brønsted acid catalysis: study of a Petasis‒Ferrier-type rearrangement catalyzed by chiral phosphoric acids
Kanomata, Kyohei; Toda, Yasunori; Shibata, Yukihiro; Yamanaka, Masahiro; Tsuzuki, Seiji; Gridnev, Ilya D.; Terada, Masahiro; Chemical Science 5 (2014) 3515–; doi:10.1039/C4SC00611A

data_1517327
_publ_section_title
;
 Secondary stereocontrolling interactions in chiral Br\/onsted acid
 catalysis: study of a Petasis--Ferrier-type rearrangement catalyzed by
 chiral phosphoric acids
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              3515
_journal_paper_doi               10.1039/C4SC00611A
_journal_volume                  5
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H24 O4'
_chemical_formula_sum            'C25 H24 O4'
_chemical_formula_weight         388.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.108(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.0714(8)
_cell_length_b                   17.224(2)
_cell_length_c                   19.620(3)
_cell_measurement_reflns_used    17176
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      3.10
_cell_volume                     2036.0(5)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 6.827
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22409
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     523
_refine_ls_number_reflns         4818
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0687P)^2^+0.3310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1437
_reflns_number_gt                3136
_reflns_number_total             4818
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_duplicate_entry             1516033
_cod_data_source_file            c4sc00611a2.cif
_cod_data_source_block           03
_cod_database_code               1517327