Development of a Nazarov Cyclization/Wagner-Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles
Jie Huang; Alison J. Frontier; Journal of the American Chemical Society 129 (2007) 8060–8061; doi:10.1021/ja0716148

data_4109614
_publ_section_title
;
 Development of a Nazarov Cyclization/Wagner-Meerwein Rearrangement
 Sequence for the Stereoselective Synthesis of Spirocycles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8060
_journal_page_last               8061
_journal_paper_doi               10.1021/ja0716148
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C21 H26 O6'
_chemical_formula_sum            'C21 H26 O6'
_chemical_formula_weight         374.42
_chemical_name_common            frojh01
_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                75.203(2)
_cell_angle_beta                 89.945(2)
_cell_angle_gamma                78.979(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9470(12)
_cell_length_b                   9.8537(17)
_cell_length_c                   14.900(3)
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      30.77
_cell_measurement_theta_min      2.18
_cell_volume                     966.7(3)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'APEX2, Bruker'
_computing_data_reduction        'SAINT, BRuker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97, CNR-IC'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14449
_diffrn_reflns_theta_full        29.56
_diffrn_reflns_theta_max         29.56
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9706
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.1872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                4444
_reflns_number_total             5388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0716148si20070306_041413.cif
_cod_data_source_block           frojh01
_cod_database_code               4109614