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_1517483
_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            'C20 H26 N2 O5'
_chemical_formula_weight         374.43
_space_group_IT_number           2
_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                77.070(5)
_cell_angle_beta                 84.753(5)
_cell_angle_gamma                87.947(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9804(7)
_cell_length_b                   9.8900(9)
_cell_length_c                   12.2837(11)
_cell_measurement_temperature    296(2)
_cell_volume                     940.85(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14600
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.095
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.003(7)
_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   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0938
_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^)+(0.1511P)^2^+2.3156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2686
_refine_ls_wR_factor_ref         0.2705
_reflns_number_gt                3152
_reflns_number_total             3275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502213w_si_003.cif
_cod_data_source_block           cvs_885
_cod_depositor_comments
'Adding full bibliography for 1517483--1517484.cif.'
_cod_database_code               1517483