Domino Imino-Aldol-Aza-Michael Reaction: One-Pot Diastereo- and Enantioselective Synthesis of Piperidines
Manas K. Ghorai; Sandipan Halder; Raj Kumar Das; Journal of Organic Chemistry 75 (2010) 7061–7072; doi:10.1021/jo101680f

data_4025779
_publ_section_title
;
 Domino Imino-Aldol-Aza-Michael Reaction: One-Pot Diastereo- and
 Enantioselective Synthesis of Piperidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7061
_journal_page_last               7072
_journal_paper_doi               10.1021/jo101680f
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C26 H31 N O5 S'
_chemical_formula_weight         469.58
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.443(5)
_cell_angle_beta                 98.737(4)
_cell_angle_gamma                94.167(6)
_cell_formula_units_Z            2
_cell_length_a                   8.179(5)
_cell_length_b                   9.871(4)
_cell_length_c                   15.334(6)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.11
_cell_volume                     1196.9(10)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 97'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6943
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0694
_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^)+(0.0916P)^2^+0.9345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1966
_reflns_number_gt                3555
_reflns_number_total             4835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101680f_si_002_4.cif
_cod_data_source_block           Compound12a
_cod_database_code               4025779