Enantio- and Diastereoselective Carbonyl-Ene Cyclization–Acetalization Tandem Reaction Catalyzed by Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acids
Ishihara, Hideyuki; Huang, Jianhao; Mochizuki, Takuya; Hatano, Manabu; Ishihara, Kazuaki; ACS Catalysis 11 (2021) 6121–6127; doi:10.1021/acscatal.1c01242

data_4518688
_publ_section_title
;
 Enantio- and Diastereoselective Carbonyl-Ene Cyclization--Acetalization
 Tandem Reaction Catalyzed by Tris(pentafluorophenyl)borane-Assisted
 Chiral Phosphoric Acids
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              6121
_journal_page_last               6127
_journal_paper_doi               10.1021/acscatal.1c01242
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration (2S,4aS,7aR)
_chemical_formula_sum            'C17 H23 Br O2'
_chemical_formula_weight         339.26
_chemical_name_common
;
(2S,4aS,7aR)-2-(3-bromophenyl)-4,4,7,7-
tetramethylhexahydrocyclopenta[d][1,3]dioxine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9557(9)
_cell_length_b                   10.9058(17)
_cell_length_c                   24.740(4)
_cell_measurement_reflns_used    5613
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.097
_cell_volume                     1606.9(4)
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Rigaku CrystalStructure'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12662
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.440
_diffrn_reflns_theta_min         3.097
_exptl_absorpt_coefficient_mu    2.558
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0282P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0646
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3125
_reflns_number_total             3624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01242_si_002.cif
_cod_data_source_block           CrystalClear
_cod_depositor_comments          'Adding full bibliography for 4518688.cif.'
_cod_database_code               4518688
_shelx_estimated_absorpt_t_min   0.629
_shelx_estimated_absorpt_t_max   0.629
_shelxl_version_number           2014/6
_shelx_res_checksum              62098
_shelx_hkl_checksum              12809