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_4115274
_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         'C23 H21 N O4 '
_chemical_formula_sum            'C23 H21 N O4'
_chemical_formula_weight         375.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                92.12(2)
_cell_angle_beta                 101.38(2)
_cell_angle_gamma                91.17(2)
_cell_formula_units_Z            2
_cell_length_a                   11.656(2)
_cell_length_b                   12.003(2)
_cell_length_c                   7.257(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      13.2
_cell_measurement_theta_min      10.5
_cell_volume                     994.3(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SAPI91
_diffrn_measured_fraction_theta_full 0.8160
_diffrn_measured_fraction_theta_max 0.8160
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.115
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2270
_diffrn_reflns_theta_full        22.48
_diffrn_reflns_theta_max         22.48
_diffrn_standards_decay_%        0.19
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       0.001(4)
_refine_ls_extinction_method     'Zachariasen(1967) type 2 gaussian isotropic'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     338
_refine_ls_number_reflns         2117
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.1657
_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         0.1778
_reflns_number_gt                590
_reflns_number_total             2117
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja0274047-4_s2_4.cif
_cod_data_source_block           7fE
_cod_original_cell_volume        994.2(4)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C23 H21 N O4 '
_cod_database_code               4115274