Diastereoselective Aminooxygenation and Diamination of Alkenes with Amidines by Hypervalent Iodine(III) Reagents.
Chen, Hui; Kaga, Atsushi; Chiba, Shunsuke; Organic letters 16 (2014) 6136–; doi:10.1021/ol503000c

data_1518694
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_section_title
;
 Diastereoselective Aminooxygenation and Diamination of Alkenes with
 Amidines by Hypervalent Iodine(III) Reagents.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6136
_journal_paper_doi               10.1021/ol503000c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C22 H20 N2'
_chemical_formula_weight         312.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 93.168(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.6185(16)
_cell_length_b                   5.5769(3)
_cell_length_c                   18.4042(8)
_cell_measurement_reflns_used    2313
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      31.0443
_cell_measurement_theta_min      2.5806
_cell_volume                     3240.3(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12552
_diffrn_reflns_theta_full        31.14
_diffrn_reflns_theta_max         31.14
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.5178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1427
_reflns_number_gt                3988
_reflns_number_total             5161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503000c_si_008.cif
_cod_data_source_block           I
_cod_database_code               1518694
_shelx_res_checksum              56311
_shelx_hkl_checksum              11152