Stereoselective Approach to cis-2,3-Disubstituted Piperidines via Reduction of N-Acyliminium Ion Intermediate: Enantioselective Synthesis of (+)-(2S,3S)-CP-99,994
Prakash R. Sultane; Ramakrishna G. Bhat; Journal of Organic Chemistry 77 (2012) 11349–11354; doi:10.1021/jo302181k

data_4027787
_publ_section_title
;
 Stereoselective Approach to cis-2,3-Disubstituted Piperidines via
 Reduction of N-Acyliminium Ion Intermediate: Enantioselective Synthesis
 of (+)-(2S,3S)-CP-99,994
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11349
_journal_page_last               11354
_journal_paper_doi               10.1021/jo302181k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C27 H28 N2 O4'
_chemical_formula_weight         444.51
_space_group_IT_number           14
_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                90.00
_cell_angle_beta                 92.642(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7606(14)
_cell_length_b                   21.095(3)
_cell_length_c                   9.8744(13)
_cell_measurement_temperature    296(2)
_cell_volume                     2239.1(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_sigmaI/netI    0.1271
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21534
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       needles
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0619
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1820
_reflns_number_gt                2645
_reflns_number_total             5408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302181k_si_001.cif
_cod_data_source_block           prs
_cod_original_cell_volume        2239.0(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027787