Tuning the Regioselectivity of Gold-Catalyzed Internal Nitroalkyne Redox: A Cycloisomerization and [3 + 2]-Cycloaddition Cascade for the Construction of spiro-Pseudoindoxyl Skeleton.
Suneel Kumar, Chepuri V.; Ramana, Chepuri V.; Organic letters 16 (2014) 4766–4769; doi:10.1021/ol502213w

data_1517484
_publ_section_title
;
 Tuning the Regioselectivity of Gold-Catalyzed Internal Nitroalkyne Redox:
 A Cycloisomerization and [3 + 2]-Cycloaddition Cascade for the
 Construction of spiro-Pseudoindoxyl Skeleton.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4766
_journal_page_last               4769
_journal_paper_doi               10.1021/ol502213w
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C25 H26 N2 O5'
_chemical_formula_weight         434.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 123.531(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.4774(18)
_cell_length_b                   8.7506(6)
_cell_length_c                   17.7496(12)
_cell_measurement_temperature    296(2)
_cell_volume                     3428.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15791
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.118
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00064(19)
_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   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0335P)^2^+3.9132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2634
_reflns_number_total             3027
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502213w_si_002.cif
_cod_data_source_block           cvs_892_r_0m
_cod_depositor_comments
'Adding full bibliography for 1517483--1517484.cif.'
_cod_database_code               1517484