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_4108393
_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_moiety         'C18 H24 O5'
_chemical_formula_sum            'C18 H24 O5'
_chemical_formula_weight         320.37
_chemical_name_common            PIIV09
_chemical_name_systematic
;
 dimethyl
 6-acetyl-7-methyl-4-methylideneoctahydroazulene-2,2(1H)-
 dicarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 75.89(3)
_cell_angle_gamma                80.67(3)
_cell_formula_units_Z            2
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_cell_length_b                   8.8546(18)
_cell_length_c                   12.460(3)
_cell_measurement_reflns_used    3554
_cell_measurement_temperature    211(2)
_cell_measurement_theta_max      23.9
_cell_measurement_theta_min      2.4
_cell_volume                     832.4(4)
_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 0.888
_diffrn_measured_fraction_theta_max 0.888
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5037
_diffrn_reflns_theta_full        24.14
_diffrn_reflns_theta_max         24.14
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (R.H. Blessing, (1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
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_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0746P)^2^+0.0020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                1947
_reflns_number_total             2366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja803691p_si_001.cif
_cod_data_source_block           Y:\PIIV09\piiv09a.CIF
_cod_original_cell_volume        832.5(3)
_cod_database_code               4108393