Intermolecular Rhodium-Catalyzed [3+2+2] Carbocyclization of Alkenylidenecyclopropanes with Activated Alkynes: Regio- and Diastereoselective Construction of cis-Fused Bicycloheptadienes
P. Andrew Evans; Phillip A. Inglesby; Journal of the American Chemical Society 130 (2008) 12838–12839; doi:10.1021/ja803691p

data_4108394
_publ_section_title
;
 Intermolecular Rhodium-Catalyzed [3+2+2] Carbocyclization of
 Alkenylidenecyclopropanes with Activated Alkynes: Regio- and
 Diastereoselective Construction of cis-Fused Bicycloheptadienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12838
_journal_page_last               12839
_journal_paper_doi               10.1021/ja803691p
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C18 H24 O5'
_chemical_formula_weight         320.37
_chemical_name_common            PIIV15
_chemical_name_systematic
;
 dimethyl
 6-acetyl-3a-methyl-8-methylideneoctahydroazulene-
 2,2(1H)-dicarboxylate
;
_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                 103.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.651(3)
_cell_length_b                   11.617(2)
_cell_length_c                   11.148(2)
_cell_measurement_reflns_used    1773
_cell_measurement_temperature    211(2)
_cell_measurement_theta_max      23.9
_cell_measurement_theta_min      2.3
_cell_volume                     1717.4(6)
_computing_cell_refinement       'IPDS (Stoe & Cie, 1996)'
_computing_data_collection       'IPDS (Stoe & Cie, 1996)'
_computing_data_reduction        'IPDS (Stoe & Cie, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      211(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       '200\% f scan, \f-incr 2.0 \%, 100 exposures'
_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  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10244
_diffrn_reflns_theta_full        24.11
_diffrn_reflns_theta_max         24.11
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (R.H. Blessing, (1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.832
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0461P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                1487
_reflns_number_total             2583
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja803691p_si_002.cif
_cod_data_source_block           y:\piiv15\piiv15t
_cod_original_cell_volume        1717.3(6)
_cod_database_code               4108394