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_4105204
_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_formula_sum            'C27 H33 N O5'
_chemical_formula_weight         451.54
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.822(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.012(3)
_cell_length_b                   9.305(2)
_cell_length_c                   22.056(5)
_cell_measurement_reflns_used    1240
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      20.23
_cell_measurement_theta_min      2.29
_cell_volume                     2412.9(10)
_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 1.000
_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  0.0893
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18592
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      0
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_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          0.1323
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                2609
_reflns_number_total             4245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9066282_si_004.cif
_cod_data_source_block           dgc915s
_cod_database_code               4105204