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_4026575
_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 H17 N O4 S'
_chemical_formula_sum            'C12 H17 N O4 S'
_chemical_formula_weight         271.33
_chemical_name_systematic
;
(4S,5R)-5-(benzyloxy)-4-methyl-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                   5.2154(3)
_cell_length_b                   11.7483(6)
_cell_length_c                   21.7737(15)
_cell_measurement_reflns_used    3990
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.1
_cell_measurement_theta_min      7.2
_cell_volume                     1334.12(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      200(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10067
_diffrn_reflns_theta_full        72.11
_diffrn_reflns_theta_max         72.11
_diffrn_reflns_theta_min         7.17
_exptl_absorpt_coefficient_mu    2.233
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881;1005 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_coef       0.0046(10)
_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   1.203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0664
_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^)+(0.0835P)^2^+0.1496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.2044
_reflns_number_gt                1677
_reflns_number_total             2554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201209x_si_002_1.cif
_cod_data_source_block           compound_5
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4026575