Enantioselective Organocatalytic Friedel-Crafts Alkylation Reaction of Indoles with 5-Hydroxyfuran-2(5H)-one: Access to Chiral γ-Lactones and γ-Lactams via a Ugi 4-Center 3-Component Reaction
Emmanuel Riguet; Journal of Organic Chemistry 76 (2011) 8143–8150; doi:10.1021/jo201184p

data_4026632
_publ_section_title
;
 Enantioselective Organocatalytic Friedel-Crafts Alkylation Reaction of
 Indoles with 5-Hydroxyfuran-2(5H)-one: Access to Chiral \g-Lactones and
 \g-Lactams via a Ugi 4-Center 3-Component Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8143
_journal_page_last               8150
_journal_paper_doi               10.1021/jo201184p
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H30 Cl3 N3 O2'
_chemical_formula_weight         522.88
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1147(2)
_cell_length_b                   15.1214(2)
_cell_length_c                   17.1572(3)
_cell_measurement_reflns_used    5463
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.57
_cell_measurement_theta_min      3.90
_cell_volume                     2624.17(8)
_computing_cell_refinement
'CrysAlisPro (Oxford Diffraction Ltd.,Version 1.171.34.44, 2010)'
_computing_data_collection
'CrysAlisPro (Oxford Diffraction Ltd.,Version 1.171.34.44, 2010)'
_computing_data_reduction
'CrysAlisPro (Oxford Diffraction Ltd.,Version 1.171.34.44, 2010)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27067
_diffrn_reflns_theta_full        76.57
_diffrn_reflns_theta_max         76.57
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    3.385
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0549P)^2^+1.0525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                4990
_reflns_number_total             5463
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201184p_si_001.cif
_cod_data_source_block           er480001
_cod_database_code               4026632