Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-yne/ene-vinylcyclopropanes and CO: homologous Pauson-Khand reaction and total synthesis of (+/-)-alpha-agarofuran.
Jiao, Lei; Lin, Mu; Zhuo, Lian-Gang; Yu, Zhi-Xiang; Organic letters 12 (2010) 2528–2531; doi:10.1021/ol100625e

data_1502957
_publ_section_title
;
 Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of
 1-yne/ene-vinylcyclopropanes and CO: homologous Pauson-Khand reaction and
 total synthesis of (+/-)-alpha-agarofuran.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2528
_journal_page_last               2531
_journal_paper_doi               10.1021/ol100625e
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        Synthetic
_chemical_formula_moiety         'C21 H24 N4 O6'
_chemical_formula_sum            'C21 H24 N4 O6'
_chemical_formula_weight         428.44
_chemical_melting_point          428
_chemical_name_common            'Bicyclic enone'
_chemical_name_systematic
'(2R,4aR,E)-methyl 7-(2-(2,4-dinitrophenyl)hydrazono)-8-methyl-4a-vinyl-1,2,3,4,4a,5,6,7-octahydronaphthalene-2-carboxylate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8464(16)
_cell_length_b                   7.4777(15)
_cell_length_c                   34.944(7)
_cell_measurement_reflns_used    17223
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      5.07
_cell_volume                     2048.5(7)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            17223
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         5.07
_diffrn_source                   'rotating anode'
_diffrn_source_type              X-ray
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  0.8887
_exptl_absorpt_correction_T_min  0.7240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T. Higashi, June 3, 2003'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method 'From ethyl acetate/dichloromethane'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0018(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   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3704
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0826P)^2^+0.1665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                2712
_reflns_number_total             3704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100625e_si_001.cif
_cod_data_source_block           sx2728
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1502957