Pd(0)/InI-mediated allylic additions to 4-acetoxy-2-azetidinone: new route to highly functionalized carbocyclic scaffolds.
Cesario, Cara; Miller, Marvin J.; Organic letters 11 (2009) 1293–1295; doi:10.1021/ol9000685

data_1503810
_publ_section_title
;
 Pd(0)/InI-mediated allylic additions to 4-acetoxy-2-azetidinone: new
 route to highly functionalized carbocyclic scaffolds.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1293
_journal_page_last               1295
_journal_paper_doi               10.1021/ol9000685
_journal_volume                  11
_journal_year                    2009
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C16 H18 N2 O3'
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 95.032(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.4692(16)
_cell_length_b                   5.0982(3)
_cell_length_c                   9.8276(6)
_cell_measurement_reflns_used    7106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4484
_cell_measurement_theta_min      2.2329
_cell_volume                     1370.99(14)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker X8 Apex II CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31993
_diffrn_reflns_theta_full        30.76
_diffrn_reflns_theta_max         30.76
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0529P)^2^+0.6461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                3278
_reflns_number_total             4244
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9000685_si_002.cif
_cod_data_source_block           bcn360_1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503810