Diastereoselective Bromocyclization of O-Allyl-N-tosyl-hydroxylamines
Boris Egart; Dieter Lentz; Constantin Czekelius; Journal of Organic Chemistry 78 (2013) 2490–2499; doi:10.1021/jo3026725

data_4028040
_publ_section_title
;
 Diastereoselective Bromocyclization of O-Allyl-N-tosyl-hydroxylamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2490
_journal_page_last               2499
_journal_paper_doi               10.1021/jo3026725
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C14 H18 Br N O3 S'
_chemical_formula_weight         360.26
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_symmetry_cell_setting           triclinic
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_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 88.577(3)
_cell_angle_gamma                74.232(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5229(11)
_cell_length_b                   9.9379(15)
_cell_length_c                   10.5460(15)
_cell_measurement_reflns_used    976
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.6
_cell_volume                     742.02(19)
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_collection       'SMART (Bruker-AXS)'
_computing_data_reduction        'SAINT (BRUKER-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       'omega scan'
_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  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9315
_diffrn_reflns_theta_full        30.59
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    2.917
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-Bruker-AXS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.2320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0633
_reflns_number_gt                3754
_reflns_number_total             4220
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3026725_si_003.cif
_cod_data_source_block           be437_1a
_cod_database_code               4028040