Development of a Formal [4 + 1] Cycloaddition: Pd(OAc)2-Catalyzed Intramolecular Cyclopropanation of 1,3-Dienyl β-Keto Esters and MgI2-Promoted Vinylcyclopropane-Cyclopentene Rearrangement
Rockford W. Coscia; Tristan H. Lambert; Journal of the American Chemical Society 131 (2009) 2496–2498; doi:10.1021/ja809226x

data_4103956
_publ_section_title
;
 Development of a Formal [4 + 1] Cycloaddition: Pd(OAc)2-Catalyzed
 Intramolecular Cyclopropanation of 1,3-Dienyl \b-Keto Esters and
 MgI2-Promoted Vinylcyclopropane-Cyclopentene Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2496
_journal_page_last               2498
_journal_paper_doi               10.1021/ja809226x
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C13 H18 O3'
_chemical_formula_weight         222.27
_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                 90.2930(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3469(4)
_cell_length_b                   14.3509(7)
_cell_length_c                   10.0116(5)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      32.52
_cell_measurement_theta_min      2.44
_cell_volume                     1199.23(10)
_computing_cell_refinement       'Bruker SMART'
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20305
_diffrn_reflns_theta_full        32.64
_diffrn_reflns_theta_max         32.64
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0626P)^2^+0.2184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                3825
_reflns_number_total             4204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809226x_si_001.cif
_cod_data_source_block           rcs10
_cod_database_code               4103956