Iodine(III)-Mediated Umpolung of Bromide Salts for the Ethoxybromination of Enamides.
Nocquet-Thibault, Sophie; Retailleau, Pascal; Cariou, Kevin; Dodd, Robert H.; Organic letters 15 (2013) 1842–1845; doi:10.1021/ol400453b

data_1511907
_publ_section_title
;
 Iodine(III)-Mediated Umpolung of Bromide Salts for the Ethoxybromination
 of Enamides.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1842
_journal_page_last               1845
_journal_paper_doi               10.1021/ol400453b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C16 H22 Br N O5 S'
_chemical_formula_sum            'C16 H22 Br N O5 S'
_chemical_formula_weight         420.32
_chemical_name_systematic
; 
 rac (2S,3R)-methyl 3-(N-allyl-4-methylphenylsulfonamido)
-2-bromo-3-ethoxypropanoate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 98.010(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.334(2)
_cell_length_b                   17.631(4)
_cell_length_c                   13.162(3)
_cell_measurement_reflns_used    784
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.726
_cell_measurement_theta_min      0.407
_cell_volume                     1915.1(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.910
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_sigmaI/netI    0.1086
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2644
_diffrn_reflns_theta_full        22.03
_diffrn_reflns_theta_max         22.03
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.279
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.231
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881;745 Bijvoet pairs'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0855
_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^)+(0.1546P)^2^+1.3364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2372
_reflns_number_gt                1523
_reflns_number_total             1823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400453b_si_002.cif
_cod_data_source_block           compound_1c
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1511907