Halonium-Initiated C-O Bond Formation via Umpolung of α-Carbon to the Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones.
Wei, Ying; Lin, Shaoxia; Xue, Hongxun; Liang, Fushun; Zhao, Baozhong; Organic letters 14 (2012) 712–715; doi:10.1021/ol203183k

data_1503570
_publ_section_title
;
 Halonium-Initiated C-O Bond Formation via Umpolung of \a-Carbon to the
 Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              712
_journal_page_last               715
_journal_paper_doi               10.1021/ol203183k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C29 H28 N2 O5 S0'
_chemical_formula_weight         484.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.367(9)
_cell_angle_beta                 109.546(8)
_cell_angle_gamma                102.862(9)
_cell_formula_units_Z            2
_cell_length_a                   8.7624(7)
_cell_length_b                   12.4446(16)
_cell_length_c                   12.7515(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1220.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       '\f and \w 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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8054
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.012(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   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0713P)^2^+0.0489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1509
_reflns_number_gt                3036
_reflns_number_total             4774
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203183k_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1503570