Palladium Catalyzed Tandem Ring Opening-Ring Closing Reaction of Diazabicyclic Alkenes: A Facile One Pot Strategy for Cyclopentannulation of Heterocycles
Jubi John; Indu U.; Eringathodi Suresh; K. V. Radhakrishnan; Journal of the American Chemical Society 131 (2009) 5042–5043; doi:10.1021/ja900477e

data_4104176
_publ_section_title
;
 Palladium Catalyzed Tandem Ring Opening-Ring Closing Reaction of
 Diazabicyclic Alkenes: A Facile One Pot Strategy for Cyclopentannulation
 of Heterocycles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5042
_journal_page_last               5043
_journal_paper_doi               10.1021/ja900477e
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C21 H28 N2 O5'
_chemical_formula_weight         388.45
_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                 106.351(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.853(4)
_cell_length_b                   19.502(7)
_cell_length_c                   9.979(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2213.4(13)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10991
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.235
_refine_ls_R_factor_all          0.1741
_refine_ls_R_factor_gt           0.1168
_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^)+(0.0743P)^2^+1.2207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2431
_reflns_number_gt                2503
_reflns_number_total             3888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja900477e_si_002.cif
_cod_data_source_block           kvrbf
_cod_original_cell_volume        2213.5(13)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4104176