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_4027260
_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         'C5 H5 N O5 S'
_chemical_formula_sum            'C5 H5 N O5 S'
_chemical_formula_weight         191.16
_chemical_name_common            aziridino-\g-lactone
_chemical_name_systematic
; 
(2aS,2a1R,5aS)-tetrahydro-2H-1,4-dioxa-3-thia-2b-
azacyclopropa[hi]inden-2-one 3,3-dioxide
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.465(4)
_cell_length_b                   6.493(4)
_cell_length_c                   17.064(8)
_cell_measurement_reflns_used    953
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      0.998
_cell_volume                     716.3(7)
_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    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD 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     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5167
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 641 Friedel pairs coverage= 0.97'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.071(13)
_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   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0000P)^2^+2.7207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                1527
_reflns_number_total             1620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300468j_si_002_2.cif
_cod_data_source_block           compound_6
_cod_database_code               4027260