Highly Diastereoselective Synthesis of Tetrahydropyridines by a C-H Activation-Cyclization-Reduction Cascade
Simon Duttwyler; Colin Lu; Arnold L. Rheingold; Robert G. Bergman; Jonathan A. Ellman; Journal of the American Chemical Society 134 (2012) 4064–4067; doi:10.1021/ja2119833

data_4117603
_publ_contact_author_address
;
Department of Chemistry
Yale University
New Haven, CT 06520
United States
;
_publ_contact_author_email       jonathan.ellman@yale.edu
_publ_contact_author_name        'Jonathan A. Ellman'
_publ_section_title
;
 Highly Diastereoselective Synthesis of Tetrahydropyridines by a C-H
 Activation-Cyclization-Reduction Cascade
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4064
_journal_page_last               4067
_journal_paper_doi               10.1021/ja2119833
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C27 H29 N'
_chemical_formula_weight         367.51
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   8.6491(4)
_cell_length_b                   9.9416(4)
_cell_length_c                   24.6891(9)
_cell_measurement_reflns_used    2319
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.29
_cell_measurement_theta_min      3.58
_cell_volume                     2122.91(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9064
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0728P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2858
_reflns_number_total             3518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2119833_si_002_5.cif
_cod_data_source_block           Product_6h_polymorph_2
_cod_database_code               4117603