Bi(OTf)3-, TfOH-, and TMSOTf- Mediated, One-Pot Epoxide Rearrangement, Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)3
R. Frederick Lambert; Robert J. Hinkle; Stephen E. Ammann; Yajing Lian; Jia Liu; Shane E. Lewis; Robert D. Pike; Journal of Organic Chemistry 76 (2011) 9269–9277; doi:10.1021/jo201478d

data_4026735
_publ_contact_author_address
;Department of Chemistry
College of William and Mary
P. O. Box 8795
Williamsburg, VA 23187-8795
;
_publ_contact_author_email       rjhink@wm.edu
_publ_contact_author_fax         757-221-2715
_publ_contact_author_name        'Robert J. Hinkle'
_publ_contact_author_phone       757-221-1501
_publ_section_title
;
 Bi(OTf)3-, TfOH-, and TMSOTf- Mediated, One-Pot Epoxide Rearrangement,
 Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward
 Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)3
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9269
_journal_page_last               9277
_journal_paper_doi               10.1021/jo201478d
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C20 H22 O'
_chemical_formula_sum            'C20 H22 O'
_chemical_formula_weight         278.38
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 116.2110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.2161(3)
_cell_length_b                   5.95830(10)
_cell_length_c                   17.2485(3)
_cell_measurement_reflns_used    7233
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.41
_cell_measurement_theta_min      5.72
_cell_volume                     1587.39(5)
_computing_cell_refinement       'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2004)'
_computing_data_reduction        SAINTPLUS
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'XSHELL (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w and \y'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8161
_diffrn_reflns_theta_full        66.90
_diffrn_reflns_theta_max         66.90
_diffrn_reflns_theta_min         5.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  0.9233
_exptl_absorpt_correction_T_min  0.8672
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.17(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0505P)^2^+0.2677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0749
_reflns_number_gt                2411
_reflns_number_total             2425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201478d_si_002.cif
_cod_data_source_block           cc
_cod_database_code               4026735