Palladium-Catalyzed Allylation of Aryl Halides with Homoallyl Alcohols Bearing a Trisubstituted Double Bond: Application to Chirality Transfer from Hydroxylated Carbon to Benzylic One
Ryota Wakabayashi; Daishi Fujino; Sayuri Hayashi; Hideki Yorimitsu; Koichiro Oshima; Journal of Organic Chemistry 75 (2010) 4337–4343; doi:10.1021/jo100857d

data_4025525
_publ_contact_author             'Hideki Yorimitsu'
_publ_contact_author_email       yori@kuchem.kyoto-u.ac.jp
_publ_contact_author_fax         +81-75-753-3970
_publ_contact_author_phone       +81-75-753-4010
_publ_section_title
;
 Palladium-Catalyzed Allylation of Aryl Halides with Homoallyl Alcohols
 Bearing a Trisubstituted Double Bond: Application to Chirality Transfer
 from Hydroxylated Carbon to Benzylic One
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4337
_journal_page_last               4343
_journal_paper_doi               10.1021/jo100857d
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C21 H23 O Si'
_chemical_formula_sum            'C21 H23 O Si'
_chemical_formula_weight         319.48
_chemical_melting_point          343
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 109.472(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.054(9)
_cell_length_b                   8.076(3)
_cell_length_c                   16.130(5)
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     3691(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.1425
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17658
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9621
_exptl_absorpt_correction_T_min  0.9380
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.20(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                5558
_reflns_number_total             8179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100857d_si_002.cif
_cod_data_source_block           00401osh
_cod_database_code               4025525