A one-pot, reductive amination/6-endo-trig cyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids
Fowler, Lindsay S.; Thomas, Lynne H.; Ellis, David; Sutherland, Andrew; Chemical Communications (Cambridge, United Kingdom) 47 (2011) 6569–6571; doi:10.1039/c1cc11916h

data_7106503
_publ_section_title
;
 A one-pot, reductive amination/6-endo-trig cyclisation for the
 stereoselective synthesis of 6-substituted-4-oxopipecolic acids
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   23
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              6569
_journal_page_last               6571
_journal_paper_doi               10.1039/c1cc11916h
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_sum            'C7 H16 Cl N O4'
_chemical_formula_weight         213.66
_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_date             2010-08-04T11:10:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2209(2)
_cell_length_b                   8.9923(3)
_cell_length_c                   13.8130(4)
_cell_measurement_reflns_used    21495
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      1
_cell_volume                     1021.12(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8583
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.7
_exptl_absorpt_coefficient_mu    0.36
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'
_exptl_crystal_density_diffrn    1.39
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.0443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0639
_reflns_number_gt                2188
_reflns_number_total             2418
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1cc11916h.txt
_cod_data_source_block           lf01
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7106503