An Easy Stereoselective Access to β,γ-Aziridino α-Amino Ester Derivatives via Mannich Reaction of Benzophenone Imines of Glycine Esters with N-Sulfonyl α-Chloroaldimines
Loránd Kiss; Sven Mangelinckx; Reijo Sillanpää; Ferenc Fülöp; Norbert De Kimpe; Journal of Organic Chemistry 72 (2007) 7199–7206; doi:10.1021/jo0710634

data_4024168
_publ_section_title
;
 An Easy Stereoselective Access to \b,\g-Aziridino \a-Amino
 Ester Derivatives via Mannich Reaction of Benzophenone Imines
 of Glycine Esters with N-Sulfonyl \a-Chloroaldimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7199
_journal_page_last               7206
_journal_paper_doi               10.1021/jo0710634
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H28 N2 O4 S'
_chemical_formula_sum            'C27 H28 N2 O4 S'
_chemical_formula_weight         476.57
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_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
_cell_angle_alpha                90
_cell_angle_beta                 107.649(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8141(6)
_cell_length_b                   25.3685(15)
_cell_length_c                   9.6924(3)
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     2533.8(2)
_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_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.94
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8063
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0737
_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^)+(0.0156P)^2^+3.4944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1505
_reflns_number_gt                3329
_reflns_number_total             4676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0710634-File003_2.cif
_cod_data_source_block           lk173=19ab
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024168