Stereocontrol of 1,5-related stereocentres using an intermediate silyl group?the diastereoselectivity of nucleophilic attack on a double bond adjacent to a stereogenic centre carrying a silyl group
Fleming, Ian; Maiti, Pranab; Ramarao, Chandrashekar; Organic & Biomolecular Chemistry 1 (2003) 3989–; doi:10.1039/b305880h

data_7151492
_publ_section_title
;
 Stereocontrol of 1,5-related stereocentres using an intermediate silyl
 group?the diastereoselectivity of nucleophilic attack on a double bond
 adjacent to a stereogenic centre carrying a silyl group
;
_journal_issue                   22
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              3989
_journal_paper_doi               10.1039/b305880h
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C28 H34 N2 O7 Si'
_chemical_formula_sum            'C28 H34 N2 O7 Si'
_chemical_formula_weight         538.66
_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                   7.5858(1)
_cell_length_b                   8.4440(1)
_cell_length_c                   43.4801(7)
_cell_measurement_reflns_used    19904
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      22.46
_cell_measurement_theta_min      1.02
_cell_volume                     2785.10(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor, 1997)
;
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Thin slice \w and \f 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  0.0738
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            10681
_diffrn_reflns_theta_full        22.59
_diffrn_reflns_theta_max         22.59
_diffrn_reflns_theta_min         3.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav Blessing (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.19(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0283P)^2^+0.7556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                2744
_reflns_number_total             3281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b305880h.txt
_cod_data_source_block           if0201
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7151492