Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylation
Bai-Lin Lei; Chang-Hua Ding; Xiao-Fei Yang; Xiao-Long Wan; Xue-Long Hou; Journal of the American Chemical Society 131 (2009) 18250–18251; doi:10.1021/ja9082717

data_4105507
_publ_section_title
;
 Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by
 Palladium-Catalyzed Asymmetric Allylic Alkylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18250
_journal_page_last               18251
_journal_paper_doi               10.1021/ja9082717
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C20 H18 Br N O2'
_chemical_formula_weight         384.26
_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                 98.428(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4204(14)
_cell_length_b                   13.393(2)
_cell_length_c                   17.560(3)
_cell_measurement_reflns_used    2212
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.937
_cell_measurement_theta_min      4.690
_cell_volume                     1726.3(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  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9993
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    2.393
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5277
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.387
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0176(10)
_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   0.826
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0533P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                2007
_reflns_number_total             3759
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9082717_si_002.cif
_cod_data_source_block           cd29488
_cod_original_cell_volume        1726.2(5)
_cod_database_code               4105507