Synthesis of Highly Enantioenriched 3,4-Dihydroquinolin-2-ones by 6-Exo-trig Radical Cyclizations of Axially Chiral α-Halo-ortho-alkenyl Anilides
David B. Guthrie; Steven J. Geib; Dennis P. Curran; Journal of the American Chemical Society 131 (2009) 15492–15500; doi:10.1021/ja9066282

data_4105203
_publ_section_title
;
 Synthesis of Highly Enantioenriched 3,4-Dihydroquinolin-2-ones by
 6-Exo-trig Radical Cyclizations of Axially Chiral \a-Halo-ortho-alkenyl
 Anilides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15492
_journal_page_last               15500
_journal_paper_doi               10.1021/ja9066282
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H28 Br N O4'
_chemical_formula_sum            'C24 H28 Br N O4'
_chemical_formula_weight         474.38
_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                 101.490(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5601(18)
_cell_length_b                   7.3873(13)
_cell_length_c                   14.727(3)
_cell_measurement_reflns_used    2752
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      22.6
_cell_measurement_theta_min      2.6
_cell_volume                     1125.8(4)
_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, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       '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  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0873
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14095
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.35
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    1.855
_exptl_absorpt_correction_T_max  0.8362
_exptl_absorpt_correction_T_min  0.6967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         7315
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.823
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                5348
_reflns_number_total             7315
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9066282_si_003.cif
_cod_data_source_block           dg81908s
_cod_original_cell_volume        1125.8(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4105203