Enantioselective Intramolecular Friedel-Crafts-Type α-Arylation of Aldehydes
K. C. Nicolaou; Rüdiger Reingruber; David Sarlah; Stefan Bräse; Journal of the American Chemical Society 131 (2009) 2086–2087; doi:10.1021/ja809405c

data_4103932
_publ_section_title
;
 Enantioselective Intramolecular Friedel-Crafts-Type \a-Arylation of
 Aldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2086
_journal_page_last               2087
_journal_paper_doi               10.1021/ja809405c
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C20 H21 Br N O4'
_chemical_formula_weight         419.29
_chemical_name_systematic
; 
 ? 
;
_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                   5.0792(10)
_cell_length_b                   15.951(3)
_cell_length_c                   24.316(5)
_cell_measurement_reflns_used    3317
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.6
_cell_volume                     1970.0(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14288
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    2.110
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate-like
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.122
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.2168
_reflns_number_gt                1972
_reflns_number_total             3441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809405c_si_002.cif
_cod_data_source_block           davs
_cod_original_cell_volume        1970.1(7)
_cod_database_code               4103932