Enantioselective Friedel-Crafts Alkylation of Indoles with Trifluoroethylidene Malonates by Copper-Bis(oxazoline) Complexes: Construction of Trifluoromethyl-Substituted Stereogenic Tertiary Carbon Center
Lele Wen; Qilong Shen; Xiaolong Wan; Long Lu; Journal of Organic Chemistry 76 (2011) 2282–2285; doi:10.1021/jo1024333

data_4026158
_publ_section_title
;
 Enantioselective Friedel-Crafts Alkylation of Indoles with
 Trifluoroethylidene Malonates by Copper-Bis(oxazoline) Complexes:
 Construction of Trifluoromethyl-Substituted Stereogenic Tertiary Carbon
 Center
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2282
_journal_page_last               2285
_journal_paper_doi               10.1021/jo1024333
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_sum            'C17 H18 F3 N O4'
_chemical_formula_weight         357.32
_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            8
_cell_length_a                   9.9910(8)
_cell_length_b                   15.5697(13)
_cell_length_c                   22.565(2)
_cell_measurement_reflns_used    4493
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.809
_cell_measurement_theta_min      4.844
_cell_volume                     3510.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20856
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5212
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.391
_exptl_crystal_size_min          0.327
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_coef       0.0010(4)
_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   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0822P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                3167
_reflns_number_total             4262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1024333_si_002.cif
_cod_data_source_block           cd29521
_cod_database_code               4026158