Hypervalent iodine mediated alkene difunctionalization of vinylphenols: diastereoselective synthesis of substituted indoles and indolizines
Kai Zhang; Hang Wang; Jingfeng Zheng; Lei Yu; Hanfeng Ding; Chem.Commun. 51 (2015) 6399–; doi:10.1039/C5cc00441A

data_7116889
_publ_section_title
;
 Hypervalent iodine mediated alkene difunctionalization of vinylphenols:
 diastereoselective synthesis of substituted indoles and indolizines
;
_journal_name_full               Chem.Commun.
_journal_page_first              6399
_journal_paper_doi               10.1039/C5cc00441A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C29 H31 N O3'
_chemical_formula_sum            'C29 H31 N O3'
_chemical_formula_weight         441.55
_chemical_name_systematic        'compound 2p'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-11 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.29(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.186(3)
_cell_length_b                   14.909(3)
_cell_length_c                   12.985(3)
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      6.10
_cell_volume                     2394.3(10)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_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      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1157
_diffrn_reflns_av_sigmaI/netI    0.0897
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18411
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5704
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.010(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   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0788
_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^)+(0.1657P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.3089
_reflns_number_gt                2362
_reflns_number_total             4215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00441a2.cif
_cod_data_source_block           1
_cod_original_cell_volume        2394.2(8)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7116889