Developing a Diastereoselective Intramolecular [4 + 3] Cycloaddition of Nitrogen-Stabilized Oxyallyl Cations Derived from N-Sulfonyl-Substituted Allenamides
Andrew G. Lohse; Richard P. Hsung; Mitchell D. Leider; Sunil K. Ghosh; Journal of Organic Chemistry 76 (2011) 3246–3257; doi:10.1021/jo200147h

data_4026243
_publ_section_title
;
 Developing a Diastereoselective Intramolecular [4 + 3] Cycloaddition of
 Nitrogen-Stabilized Oxyallyl Cations Derived from N-Sulfonyl-Substituted
 Allenamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3246
_journal_page_last               3257
_journal_paper_doi               10.1021/jo200147h
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C20 H29 N O4'
_chemical_formula_sum            'C20 H29 N O4'
_chemical_formula_weight         347.44
_chemical_name_common            08111
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.939(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.069(5)
_cell_length_b                   9.734(5)
_cell_length_c                   19.568(9)
_cell_measurement_reflns_used    2816
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.01
_cell_measurement_theta_min      2.34
_cell_volume                     1913.4(16)
_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 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_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  0.0927
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17990
_diffrn_reflns_theta_full        25.11
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       rod
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
'Flack H D (1983), 3133 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0645
_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^)+(0.0691P)^2^+0.8650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                2660
_reflns_number_total             3615
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200147h_si_002.cif
_cod_data_source_block           08111
_cod_original_cell_volume        1913.5(16)
_cod_database_code               4026243