Direct construction of bicyclic heterocycles by palladium-catalyzed domino cyclization of propargyl bromides.
Ohno, Hiroaki; Okano, Akinori; Kosaka, Shohei; Tsukamoto, Koji; Ohata, Miyo; Ishihara, Kotaro; Maeda, Hatsuo; Tanaka, Tetsuaki; Fujii, Nobutaka; Organic letters 10 (2008) 1171–1174; doi:10.1021/ol800063d

data_1504570
_publ_section_title
;
 Direct construction of bicyclic heterocycles by palladium-catalyzed
 domino cyclization of propargyl bromides.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1171
_journal_page_last               1174
_journal_paper_doi               10.1021/ol800063d
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H30 N2 O4 S2'
_chemical_formula_sum            'C24 H30 N2 O4 S2'
_chemical_formula_weight         474.62
_chemical_melting_point          447
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7896(2)
_cell_length_b                   11.2493(2)
_cell_length_c                   41.8746(8)
_cell_measurement_temperature    296(2)
_cell_volume                     5082.55(16)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 2003)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPIII (Johnson et al., 1996)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            56973
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.07
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  0.496
_exptl_absorpt_correction_T_min  0.259
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; T. Higashi, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(17)
_refine_ls_extinction_coef       0.00039(4)
_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   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         9222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0271P)^2^+2.3872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                7101
_reflns_number_total             9222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800063d-file003.cif
_cod_data_source_block           ipr6
_cod_database_code               1504570