A Novel Aryl Migration from Silicon to Carbon: An Efficient Approach to Asymmetric Synthesis of α-Aryl β-Hydroxy Cyclic Amines and Silanols
Katsuhiko Tomooka; Atsuo Nakazaki; Takeshi Nakai; Journal of the American Chemical Society 122 (2000) 408–409; doi:10.1021/ja993295t

data_4115883
_publ_contact_author
;
    Katsuhiko Tomooka
    Department of Applied Chemistry 
    Graduate School of Science and Engineering
    Tokyo Institute of Technology
    O-okayama Meguro-ku Tokyo
    152-8552 Japan
;
_publ_contact_author_email       ktomooka@o.cc.titech.ac.jp
_publ_contact_author_fax         '+81 3 5734 3931'
_publ_contact_author_phone       '+81 3 5734 2580'
_publ_section_title
;
 A Novel Aryl Migration from Silicon to Carbon: An Efficient Approach to
 Asymmetric Synthesis of \a-Aryl \b-Hydroxy Cyclic Amines and Silanols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              408
_journal_page_last               409
_journal_paper_doi               10.1021/ja993295t
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C32 H41 N O4 Si'
_chemical_formula_weight         531.75
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1818(14)
_cell_length_b                   31.962(3)
_cell_length_c                   9.4921(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     3089.0(6)
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  '4-circle diffractometer'
_diffrn_measurement_method       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4561
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         1.27
_exptl_absorpt_coefficient_mu    0.110
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       Block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.49(16)
_refine_ls_extinction_coef       0.0280(18)
_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   1.163
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                4214
_reflns_number_total             4561
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja993295t_1.cif
_cod_data_source_block           a
_cod_database_code               4115883