Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles with Donor-Acceptor Cyclopropanes
Hu Xiong; Hao Xu; Saihu Liao; Zuowei Xie; Yong Tang; Journal of the American Chemical Society 135 (2013) 7851–7854; doi:10.1021/ja4042127

data_4119820
_publ_section_title
;
 Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles
 with Donor-Acceptor Cyclopropanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7851
_journal_page_last               7854
_journal_paper_doi               10.1021/ja4042127
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H30 Br N O5'
_chemical_formula_weight         564.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.113(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8961(13)
_cell_length_b                   11.3528(11)
_cell_length_c                   17.3669(16)
_cell_measurement_reflns_used    9625
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.57
_cell_volume                     2737.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0954
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26495
_diffrn_reflns_theta_full        30.63
_diffrn_reflns_theta_max         30.63
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  0.6384
_exptl_absorpt_correction_T_min  0.5777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         1.049
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         16265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                13111
_reflns_number_total             16265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4042127_3ha.cif
_cod_data_source_block           mo_dm12594_0m
_cod_database_code               4119820