Highly Stereoselective Formal [3 + 3] Cycloaddition of Enals and Azomethine Imines Catalyzed by N-Heterocyclic Carbenes
Audrey Chan; Karl A. Scheidt; Journal of the American Chemical Society 129 (2007) 5334–5335; doi:10.1021/ja0709167

data_4109359
_publ_contact_author_email       scheidt@northwestern.edu
_publ_contact_author_name        'Karl Scheidt'
_publ_section_title
;
 Highly Stereoselective Formal [3 + 3] Cycloaddition of Enals and
 Azomethine Imines Catalyzed by N-Heterocyclic Carbenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5334
_journal_page_last               5335
_journal_paper_doi               10.1021/ja0709167
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C26 H24 N2 O2'
_chemical_formula_weight         396.47
_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                93.6650(10)
_cell_angle_beta                 95.4380(10)
_cell_angle_gamma                91.5370(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4020(7)
_cell_length_b                   10.0753(7)
_cell_length_c                   10.8800(8)
_cell_measurement_temperature    153(2)
_cell_volume                     1023.34(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9410
_diffrn_reflns_theta_full        28.82
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             420
_refine_diff_density_max         1.540
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          5.080
_refine_ls_shift/su_mean         0.051
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0960P)^2^+0.6340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1805
_reflns_number_gt                4137
_reflns_number_total             4750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0709167si20070208_105336.cif
_cod_data_source_block           Chan_Scheidt2
_cod_database_code               4109359