Aziridines from Intramolecular Alkene Aziridination of Sulfamates: Reactivity toward Carbon Nucleophiles. Application to the Synthesis of Spisulosine and Its Fluoro Analogue
Guillaume Malik; Audrey Estéoule; Pascal Retailleau; Philippe Dauban; Journal of Organic Chemistry 76 (2011) 7438–7448; doi:10.1021/jo201209x

data_4026576
_publ_section_title
;
 Aziridines from Intramolecular Alkene Aziridination of Sulfamates:
 Reactivity toward Carbon Nucleophiles. Application to the Synthesis of
 Spisulosine and Its Fluoro Analogue
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7438
_journal_page_last               7448
_journal_paper_doi               10.1021/jo201209x
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H16 F N O5 S2'
_chemical_formula_sum            'C12 H16 F N O5 S2'
_chemical_formula_weight         337.38
_chemical_name_systematic
;
(4S,5R)-5-fluoro-4-methyl-3-tosyl-1,2,3-oxathiazepane 2,2-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                   8.4810(4)
_cell_length_b                   11.2846(5)
_cell_length_c                   15.6157(11)
_cell_measurement_reflns_used    7388
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9
_cell_measurement_theta_min      6.5
_cell_volume                     1494.50(14)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16970
_diffrn_reflns_theta_full        72.15
_diffrn_reflns_theta_max         72.15
_diffrn_reflns_theta_min         6.53
_exptl_absorpt_coefficient_mu    3.538
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1202 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0024(3)
_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   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0504P)^2^+0.4369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2562
_reflns_number_total             2892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201209x_si_002_2.cif
_cod_data_source_block           compound_22
_cod_database_code               4026576