Rhodium-Catalyzed Intramolecular Formation of N-Sulfamoyl 2,3-Aziridino-γ-lactones and Their Use for the Enantiospecific Synthesis of α,β-Diamino Acid Derivatives
Marcelo Siqueira Valle; Mauricio Frota Saraiva; Pascal Retailleau; Mauro V. de Almeida; Robert H. Dodd; Journal of Organic Chemistry 77 (2012) 5592–5599; doi:10.1021/jo300468j

data_4027259
_publ_contact_author_address
;Centre de recherche de Gif-sur-Yvette
Institut de Chimie des Substances Naturelles
UPR 2301, CNRS
Avenue de la Terrasse
91198 Gif-sur-Yvette
France
;
_publ_contact_author_email       robert.dodd@icsn.cnrs-gif.fr
_publ_contact_author_fax         '+33 1 69 07 72 47 '
_publ_contact_author_name        'Robert H. Dodd'
_publ_contact_author_phone       '+33 1 69 82 45 94'
_publ_section_title
;
 Rhodium-Catalyzed Intramolecular Formation of N-Sulfamoyl
 2,3-Aziridino-\g-lactones and Their Use for the Enantiospecific Synthesis
 of \a,\b-Diamino Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5592
_journal_page_last               5599
_journal_paper_doi               10.1021/jo300468j
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H23 N3 O5 S'
_chemical_formula_sum            'C19 H23 N3 O5 S'
_chemical_formula_weight         405.46
_chemical_name_systematic
; 
(4S,5S,6S)-N-benzyl-5-(benzylamino)-6-hydroxy-1,2,3-oxathiazepane
-4-carboxamide 2,2-dioxide 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 96.127(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.998(2)
_cell_length_b                   5.5220(10)
_cell_length_c                   18.252(5)
_cell_measurement_reflns_used    2517
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.261
_cell_measurement_theta_min      0.407
_cell_volume                     2004.0(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL package (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4553
_diffrn_reflns_theta_full        21.26
_diffrn_reflns_theta_max         21.26
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       'tiny needle'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 817 Friedel pairs, cov 0.83'
_refine_ls_abs_structure_Flack   0.06(18)
_refine_ls_extinction_coef       0.0047(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+4.4698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                1637
_reflns_number_total             2088
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300468j_si_002_1.cif
_cod_data_source_block           compound_8a
_cod_database_code               4027259