Highly Selective Diels-Alder Reactions of Directly Connected Enyne Dienophiles
Mingji Dai; David Sarlah; Maolin Yu; Samuel J. Danishefsky; Gavin O. Jones; K. N. Houk; Journal of the American Chemical Society 129 (2007) 645–657; doi:10.1021/ja065762u

data_4108983
_publ_section_title
;
 Highly Selective Diels-Alder Reactions of Directly Connected Enyne
 Dienophiles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              645
_journal_page_last               657
_journal_paper_doi               10.1021/ja065762u
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C14 H16 O6'
_chemical_formula_weight         280.27
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.6220(10)
_cell_angle_beta                 87.493(2)
_cell_angle_gamma                89.2230(10)
_cell_formula_units_Z            8
_cell_length_a                   7.5383(6)
_cell_length_b                   18.2795(13)
_cell_length_c                   19.8407(13)
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      27.010
_cell_measurement_theta_min      2.315
_cell_volume                     2730.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      243(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17653
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.03
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0007(3)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         11043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0702P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                5737
_reflns_number_total             11043
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja065762usi20061107_015906.cif
_cod_data_source_block           das10
_cod_database_code               4108983