Remote Control of Diastereoselectivity in Intramolecular Reactions of Chiral Allylsilanes
Weston R. Judd; Sooho Ban; Jeffrey Aubé; Journal of the American Chemical Society 128 (2006) 13736–13741; doi:10.1021/ja063411+

data_4110992
_publ_contact_author
; 
   Prof. Jeffrey Aub\'e 
   Department of Medicinal Chemistry 
   University of Kansas 
   Malott Hall, Room 4070 
   1251 Wescoe Hall Dr. 
   Lawrence, KS  66045-7582  USA 
;
_publ_contact_author_email       jaube@ku.edu
_publ_contact_author_fax         1(785)8645326
_publ_contact_author_phone       1(785)8644496
_publ_section_title
;
 Remote Control of Diastereoselectivity in Intramolecular Reactions of
 Chiral Allylsilanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13736
_journal_page_last               13741
_journal_paper_doi               10.1021/ja063411+
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         '(C25 H25 Br N2 O5), (H2 O)0.5'
_chemical_formula_sum            'C25 H26 Br N2 O5.5'
_chemical_formula_weight         522.39
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_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                 100.593(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.280(9)
_cell_length_b                   26.196(9)
_cell_length_c                   8.466(3)
_cell_measurement_reflns_used    3440
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.38
_cell_measurement_theta_min      2.52
_cell_volume                     4639(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9883
_diffrn_reflns_theta_full        21.96
_diffrn_reflns_theta_max         21.96
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.814
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             2152
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.274
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     608
_refine_ls_number_reflns         4947
_refine_ls_number_restraints     557
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.1119
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1200P)^2^+140.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2853
_refine_ls_wR_factor_ref         0.2938
_reflns_number_gt                4222
_reflns_number_total             4947
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja063411si20060516_113508_3.cif
_cod_data_source_block           compound_20_
_cod_original_formula_sum        'C25 H26 Br N2 O5.50'
_cod_database_code               4110992