Stereoselective Intramolecular [4 + 3] Cycloadditions of Nitrogen-Stabilized Chiral Oxyallyl Cations via Epoxidation of N-Tethered Allenamides
Hui Xiong; Jian Huang; Sunil K. Ghosh; Richard P. Hsung; Journal of the American Chemical Society 125 (2003) 12694–12695; doi:10.1021/ja030416n

data_4114266
_publ_section_title
;
 Stereoselective Intramolecular [4 + 3] Cycloadditions of
 Nitrogen-Stabilized Chiral Oxyallyl Cations via Epoxidation of N-Tethered
 Allenamides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12694
_journal_page_last               12695
_journal_paper_doi               10.1021/ja030416n
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C14 H19 N O4'
_chemical_formula_sum            'C14 H19 N O4'
_chemical_formula_weight         265.30
_chemical_name_common            03081vv
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   10.9417(8)
_cell_length_b                   10.7162(8)
_cell_length_c                   11.6477(9)
_cell_measurement_reflns_used    1752
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.55
_cell_volume                     1365.73(18)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0081
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            15437
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         1653
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0677P)^2^+0.1290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                1580
_reflns_number_total             1653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja030416n_2.cif
_cod_data_source_block           03081vv
_cod_original_cell_volume        1365.7(2)
_cod_database_code               4114266