Hydrogen-Bond-Directed Highly Stereoselective Synthesis of Z-Enamides via Pd-Catalyzed Oxidative Amidation of Conjugated Olefins
Ji Min Lee; Doo-Sik Ahn; Doo Young Jung; Junseung Lee; Youngkyu Do; Sang Kyu Kim; Sukbok Chang; Journal of the American Chemical Society 128 (2006) 12954–12962; doi:10.1021/ja0639315

data_4110934
_publ_section_title
;
 Hydrogen-Bond-Directed Highly Stereoselective Synthesis of Z-Enamides via
 Pd-Catalyzed Oxidative Amidation of Conjugated Olefins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12954
_journal_page_last               12962
_journal_paper_doi               10.1021/ja0639315
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_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                100.346(2)
_cell_angle_beta                 91.249(2)
_cell_angle_gamma                117.880(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2906(10)
_cell_length_b                   8.6854(10)
_cell_length_c                   9.0243(11)
_cell_measurement_temperature    293(2)
_cell_volume                     560.85(12)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6416
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             232
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                1499
_reflns_number_total             2516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0639315si20060605_013752.cif
_cod_data_source_block           sbc54
_cod_database_code               4110934