Gold-Catalyzed Stereoselective Synthesis of Azacyclic Compounds through a Redox/[2 + 2 + 1] Cycloaddition Cascade of Nitroalkyne Substrates
Appaso Mahadev Jadhav; Sabyasachi Bhunia; Hsin-Yi Liao; Rai-Shung Liu; Journal of the American Chemical Society 133 (2011) 1769–1771; doi:10.1021/ja110514s

data_4105635
_publ_section_title
;
 Gold-Catalyzed Stereoselective Synthesis of Azacyclic Compounds through a
 Redox/[2 + 2 + 1] Cycloaddition Cascade of Nitroalkyne Substrates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1769
_journal_page_last               1771
_journal_paper_doi               10.1021/ja110514s
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.5620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3656(8)
_cell_length_b                   13.4721(9)
_cell_length_c                   7.4844(5)
_cell_measurement_reflns_used    5600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3716
_cell_measurement_theta_min      3.0241
_cell_volume                     1142.37(13)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9713
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+1.2268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                1977
_reflns_number_total             2335
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja110514s_si_001.cif
_cod_data_source_block           100836lt
_cod_database_code               4105635