Nucleophilic Dearomatization of Pyridines under Enamine Catalysis: Regio-, Diastereo-, and Enantioselective Addition of Aldehydes to Activated N-Alkylpyridinium Salts.
Bertuzzi, Giulio; Sinisi, Alessandro; Pecorari, Daniel; Caruana, Lorenzo; Mazzanti, Andrea; Bernardi, Luca; Fochi, Mariafrancesca; Organic letters 19 (2017) 834–837; doi:10.1021/acs.orglett.6b03824

data_1545451
_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
;
 Nucleophilic Dearomatization of Pyridines under Enamine Catalysis:
 Regio-, Diastereo-, and Enantioselective Addition of Aldehydes to
 Activated N-Alkylpyridinium Salts.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              834
_journal_page_last               837
_journal_paper_doi               10.1021/acs.orglett.6b03824
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H33 Cl3 N2 O4 S2'
_chemical_formula_weight         644.04
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_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   geom
_audit_creation_date             11/30/2016
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_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   10.6471(8)
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_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
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_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CMOS area detector'
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_k_min       -21
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_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
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_diffrn_reflns_theta_max         25.999
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_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       brick
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.945
_exptl_transmission_factor_min   0.851
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_refine_diff_density_min         -0.822
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_refine_ls_abs_structure_details
;
 Flack x determined using 2350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.047(11)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0735
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1458P)^2^+2.0539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2111
_refine_ls_wR_factor_ref         0.2165
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5721
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_reflns_threshold_expression     'I > 2\s(I)'
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_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.947
_shelx_res_checksum              89139
_shelx_hkl_checksum              49331