Highly Regio-, Diastereo-, and Enantioselective Pd-Catalyzed Allylic Alkylation of Acyclic Ketone Enolates with Monosubstituted Allyl Substrates
Wen-Hua Zheng; Bao-Hui Zheng; Yan Zhang; Xue-Long Hou; Journal of the American Chemical Society 129 (2007) 7718–7719; doi:10.1021/ja071098l

data_4109562
_publ_section_title
;
 Highly Regio-, Diastereo-, and Enantioselective Pd-Catalyzed Allylic
 Alkylation of Acyclic Ketone Enolates with Monosubstituted Allyl
 Substrates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7718
_journal_page_last               7719
_journal_paper_doi               10.1021/ja071098l
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C32 H32 O3'
_chemical_formula_weight         464.58
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 102.402(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.675(2)
_cell_length_b                   6.0983(13)
_cell_length_c                   22.524(5)
_cell_measurement_reflns_used    1142
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.660
_cell_measurement_theta_min      5.044
_cell_volume                     1297.9(5)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.1090
_diffrn_reflns_av_sigmaI/netI    0.1054
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7615
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77325
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_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   0.767
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.767
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                1606
_reflns_number_total             3068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071098lsi20070215_025233.cif
_cod_data_source_block           cd26392
_cod_original_cell_volume        1298.0(5)
_cod_database_code               4109562