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_4025778
_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            'C25 H25 N O6 S'
_chemical_formula_weight         467.52
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 98.037(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   9.738(5)
_cell_length_b                   29.292(4)
_cell_length_c                   8.035(6)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.11
_cell_volume                     2269(2)
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0975
_diffrn_reflns_av_sigmaI/netI    0.1180
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14783
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5548
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0664
_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^)+(0.0849P)^2^+0.5218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1927
_reflns_number_gt                3431
_reflns_number_total             5548
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101680f_si_002_3.cif
_cod_data_source_block           Compound6j
_cod_database_code               4025778