Diastereoselective Intramolecular Temporary Silicon-Tethered Rhodium-Catalyzed [4+2+2] Cycloisomerization Reactions: Regiospecific Incorporation of Substituted 1,3-Butadienes
P. Andrew Evans; Erich W. Baum; Journal of the American Chemical Society 126 (2004) 11150–11151; doi:10.1021/ja046030+

data_4112933
_publ_contact_author_address
;
        Indiana University
        Department of Chemistry
        800 E. Kirkwood Ave.
        Bloomington, IN 47405-7102
        USA
;
_publ_contact_author_email       paevans@indiana.edu
_publ_contact_author_fax         '++ 812 855 8300'
_publ_contact_author_name        'Evans, P. Andrew'
_publ_contact_author_phone       '++ 812 855 7368'
_publ_section_title
;
 Diastereoselective Intramolecular Temporary Silicon-Tethered
 Rhodium-Catalyzed [4+2+2] Cycloisomerization Reactions: Regiospecific
 Incorporation of Substituted 1,3-Butadienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11150
_journal_page_last               11151
_journal_paper_doi               10.1021/ja046030+
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C25 H37 N O3 S Si'
_chemical_formula_weight         459.71
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.199(3)
_cell_angle_beta                 84.017(3)
_cell_angle_gamma                89.845(3)
_cell_formula_units_Z            8
_cell_length_a                   8.5445(8)
_cell_length_b                   22.090(2)
_cell_length_c                   26.409(3)
_cell_measurement_reflns_used    929
_cell_measurement_temperature    112(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.60
_cell_volume                     4940.0(9)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999), XTEL (local program)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      112(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
'   0.30 degree frames measured for  15.17 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_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  0.1322
_diffrn_reflns_av_sigmaI/netI    0.1697
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            60479
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       'cleaved plate'
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.691
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1709
_refine_ls_number_reflns         22701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.691
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.377
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                11827
_reflns_number_total             22701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0460302Bsi20040708_055651.cif
_cod_data_source_block           04055
_cod_original_cell_volume        4940.1(8)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4112933