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_4115272
_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         'C21 H20 Cl N O4 '
_chemical_formula_sum            'C21 H20 Cl N O4'
_chemical_formula_weight         385.85
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 95.76(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.601(6)
_cell_length_b                   9.651(4)
_cell_length_c                   26.999(4)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      14.1
_cell_measurement_theta_min      12.6
_cell_volume                     1970.6(18)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_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_measured_fraction_theta_full 0.8515
_diffrn_measured_fraction_theta_max 0.8515
_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  0.087
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            4438
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_standards_decay_%        2.08
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_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         0.44
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3846
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.1569
_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         0.1747
_reflns_number_gt                1149
_reflns_number_total             3846
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja0274047-4_s2_2.cif
_cod_data_source_block           6bE
_cod_original_cell_volume        1970(1)
_cod_original_formula_sum        'C21 H20 Cl N O4 '
_cod_database_code               4115272