Diastereoselective Addition of γ-Substituted Allylic Nucleophiles to Ketones: Highly Stereoselective Synthesis of Tertiary Homoallylic Alcohols Using an Allylic Tributylstannane/Stannous Chloride System
Makoto Yasuda; Kay Hirata; Mitsuyoshi Nishino; Akihiro Yamamoto; Akio Baba; Journal of the American Chemical Society 124 (2002) 13442–13447; doi:10.1021/ja0274047

data_4115277
_publ_contact_author_address
;
    Department of Molecular Chemistry
    Graduate School of Engineering
    Osaka University
    2-1 Yamadaoka
    Suita Osaka 565-0871
    Japan
;
_publ_contact_author_email       ' baba@ap.chem.eng.osaka-u.ac.jp'
_publ_contact_author_fax         ' 81(6)68797387 '
_publ_contact_author_name        ' Dr Akio Baba'
_publ_contact_author_phone       ' 81(6)68797386 '
_publ_section_title
;
 Diastereoselective Addition of \g-Substituted Allylic Nucleophiles to
 Ketones: Highly Stereoselective Synthesis of Tertiary Homoallylic
 Alcohols Using an Allylic Tributylstannane/Stannous Chloride System
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13442
_journal_page_last               13447
_journal_paper_doi               10.1021/ja0274047
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C17 H22 O2 '
_chemical_formula_sum            'C17 H22 O2'
_chemical_formula_weight         258.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 96.211(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.063(2)
_cell_length_b                   16.375(2)
_cell_length_c                   5.6664(9)
_cell_measurement_reflns_used    12047
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.4
_cell_volume                     1481.7(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7439
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.011
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2209
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.6409
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2209
_reflns_number_total             3395
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja0274047-4_s2_7.cif
_cod_data_source_block           19
_cod_original_formula_sum        'C17 H22 O2 '
_cod_database_code               4115277