A Dual-Catalysis Approach to the Asymmetric Steglich Rearrangement and Catalytic Enantioselective Addition of O-Acylated Azlactones to Isoquinolines
Chandra Kanta De; Nisha Mittal; Daniel Seidel; Journal of the American Chemical Society 133 (2011) 16802–16805; doi:10.1021/ja208156z

data_4107010
_publ_section_title
;
 A Dual-Catalysis Approach to the Asymmetric Steglich Rearrangement and
 Catalytic Enantioselective Addition of O-Acylated Azlactones to
 Isoquinolines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16802
_journal_page_last               16805
_journal_paper_doi               10.1021/ja208156z
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H21 Br N2 O5'
_chemical_formula_weight         533.37
_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                 114.153(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.790(2)
_cell_length_b                   19.669(5)
_cell_length_c                   12.151(3)
_cell_measurement_reflns_used    512
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.97
_cell_measurement_theta_min      2.77
_cell_volume                     2353.0(9)
_computing_cell_refinement       'Bruker SAINT'
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20711
_diffrn_reflns_theta_full        26.79
_diffrn_reflns_theta_max         26.79
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  0.9483
_exptl_absorpt_correction_T_min  0.8139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       lathe
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         9917
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+1.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                7835
_reflns_number_total             9917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja208156z_si_003.cif
_cod_data_source_block           5-br_final
_cod_original_cell_volume        2353.1(9)
_cod_database_code               4107010