Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines.
Callebaut, Gert; Colpaert, Filip; Nonn, Melinda; Kiss, Loránd; Sillanpää, Reijo; Törnroos, Karl W; Fülöp, Ferenc; De Kimpe, Norbert; Mangelinckx, Sven; Organic & biomolecular chemistry 12 (2014) 3393–3405; doi:10.1039/c4ob00243a

data_7153748
_publ_section_title
;
 Asymmetric synthesis of chloroisothreonine derivatives via
 syn-stereoselective Mannich-type additions across
 N-sulfinyl-\a-chloroimines.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3393
_journal_page_last               3405
_journal_paper_doi               10.1039/c4ob00243a
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H28 Cl N O6 S'
_chemical_formula_weight         433.93
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 90.1980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2925(5)
_cell_length_b                   22.0931(18)
_cell_length_c                   15.8946(13)
_cell_measurement_temperature    100(2)
_cell_volume                     2209.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37001
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.8351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS G.M Sheldrick, University of 
G\"ttingen, Germany, 2008.
;
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         12989
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0696
_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^)+(0.0523P)^2^+4.9345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1860
_refine_ls_wR_factor_ref         0.1875
_reflns_number_gt                12308
_reflns_number_total             12989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00243a2.cif
_cod_data_source_block           Compound5bb
_cod_depositor_comments
'Adding full bibliography for 7153748--7153750.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7153748