Catalytic Enantioselective Addition of Indoles to ActivatedN-Benzylpyridinium Salts: Nucleophilic Dearomatization of Pyridines with Unusual C-4 Regioselectivity
Bertuzzi, Giulio; Sinisi, Alessandro; Caruana, Lorenzo; Mazzanti, Andrea; Fochi, Mariafrancesca; Bernardi, Luca; ACS Catalysis 6 (2016) 6473–; doi:10.1021/acscatal.6b01962

data_4513984
_publ_contact_author
;
Prof. Dr. Andrea Mazzanti
University of Bologna
Department of Industrial Chemistry "Toso Montanari"
Viale Risorgimento 4
40136 Bologna
Italy
;
_publ_section_title
;
 Catalytic Enantioselective Addition of Indoles to
 ActivatedN-Benzylpyridinium Salts: Nucleophilic Dearomatization of
 Pyridines with Unusual C-4 Regioselectivity
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              6473
_journal_paper_doi               10.1021/acscatal.6b01962
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H24 Cl N3 O2'
_chemical_formula_weight         421.91
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             01/16/2016
_audit_creation_method           SHELXL-2014/7
_audit_update_record             07/14/2016
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4050(4)
_cell_length_b                   14.2652(6)
_cell_length_c                   14.6935(6)
_cell_measurement_reflns_used    284
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.98
_cell_volume                     2180.95(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20389
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.990
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       plates
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1053P)^2^+0.7766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3259
_reflns_number_total             4133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01962_si_002.cif
_cod_data_source_block           5-cloro_a
_cod_database_code               4513984
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.924
_shelx_estimated_absorpt_t_max   0.997
_exptl_absorpt_special_details   'Bruker SADABS'
_shelx_res_checksum              84309
_shelx_hkl_checksum              28500