One-pot asymmetric synthesis of substituted piperidines by exocyclic chirality induction.
Chen, Yunfeng; Zhong, Cheng; Petersen, Jeffrey L.; Akhmedov, Novruz G.; Shi, Xiaodong; Organic letters 11 (2009) 2333–2336; doi:10.1021/ol900708d

data_1503938
_publ_section_title
;
 One-pot asymmetric synthesis of substituted piperidines by exocyclic
 chirality induction.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2333
_journal_page_last               2336
_journal_paper_doi               10.1021/ol900708d
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C20 H23 N3 O5'
_chemical_formula_weight         385.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.095(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3075(5)
_cell_length_b                   16.2765(9)
_cell_length_c                   12.9681(7)
_cell_measurement_reflns_used    8503
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.52
_cell_measurement_theta_min      2.20
_cell_volume                     1949.54(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12768
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.4050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1437
_reflns_number_gt                3533
_reflns_number_total             4418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900708d_si_002.cif
_cod_data_source_block           6c-major
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1503938