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_4110935
_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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 110.78(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.65(7)
_cell_length_b                   8.84(3)
_cell_length_c                   10.87(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1136(9)
_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 0.924
_diffrn_measured_fraction_theta_max 0.924
_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  0.0889
_diffrn_reflns_av_sigmaI/netI    0.1364
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6455
_diffrn_reflns_theta_full        28.13
_diffrn_reflns_theta_max         28.13
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             464
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.020(5)
_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   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.2466
_refine_ls_R_factor_gt           0.0929
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0959P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2623
_reflns_number_gt                733
_reflns_number_total             2574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0639315si20060605_013812.cif
_cod_data_source_block           sbc55
_cod_database_code               4110935