Asymmetric synthesis of γ-chloro-α,β-diamino- and β,γ-aziridino-α-aminoacylpyrrolidines and -piperidines via stereoselective Mannich-type additions of N-(diphenylmethylene)glycinamides across α-chloro-N-sulfinylimines.
Callebaut, Gert; Mangelinckx, Sven; Van der Veken, Pieter; Törnroos, Karl W; Augustyns, Koen; De Kimpe, Norbert; Beilstein journal of organic chemistry 8 (2012) 2124–2131; doi:10.3762/bjoc.8.239

data_4029717
_publ_section_title
;
 Asymmetric synthesis of \g-chloro-\a,\b-diamino- and
 \b,\g-aziridino-\a-aminoacylpyrrolidines and -piperidines via
 stereoselective Mannich-type additions of
 N-(diphenylmethylene)glycinamides across \a-chloro-N-sulfinylimines.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              2124
_journal_page_last               2131
_journal_paper_doi               10.3762/bjoc.8.239
_journal_volume                  8
_journal_year                    2012
_chemical_formula_sum            'C31 H36 Cl N3 O2 S'
_chemical_formula_weight         550.14
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 105.8580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4511(7)
_cell_length_b                   9.1426(6)
_cell_length_c                   16.1139(11)
_cell_measurement_temperature    123(2)
_cell_volume                     1481.09(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9757
_diffrn_reflns_theta_full        32.07
_diffrn_reflns_theta_max         32.07
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.9406
_exptl_absorpt_correction_T_min  0.7791
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          1.14
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         9757
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0595
_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^)+(0.1059P)^2^+0.1801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1523
_reflns_number_gt                9521
_reflns_number_total             9757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-8-239-S2.cif
_cod_data_source_block           gc241
_cod_database_code               4029717