Diastereoselective Ritter Reactions of Chiral CyclicN-Acyliminium Ions: Synthesis of Pyrido- and Pyrrolo[2,3-d]oxazoles and 4-Hydroxy-5-N-acylaminopyrrolidines and 5-Hydroxy-6-N-acylaminopiperidines
Morgan, Ian R.; Yazici, Arife; Pyne, Stephen G.; Skelton, Brian W.; The Journal of Organic Chemistry 73 (2008) 2943–2946; doi:10.1021/jo800007g

data_4028910
_publ_section_title
;
 Diastereoselective Ritter Reactions of Chiral CyclicN-Acyliminium
 Ions:&#x00A0; Synthesis of Pyrido- and Pyrrolo[2,3-d]oxazoles and
 4-Hydroxy-5-N-acylaminopyrrolidines and
 5-Hydroxy-6-N-acylaminopiperidines
;
_journal_issue                   7
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              2943
_journal_page_last               2946
_journal_paper_doi               10.1021/jo800007g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C13 H17 N O4'
_chemical_formula_sum            'C13 H17 N O4'
_chemical_formula_weight         251.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-09-03T14:46:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.57(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.334(3)
_cell_length_b                   11.0540(10)
_cell_length_c                   10.822(3)
_cell_measurement_reflns_used    5399
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8546
_cell_measurement_theta_min      2.6172
_cell_volume                     1232.3(5)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
        (compiled Jun 12 2006,17:01:16)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
        (compiled Jun 12 2006,17:01:16)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
        (compiled Jun 12 2006,17:01:16)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.0009
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
;
 Oxford Diffraction Xcalibur diffractometer
;
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0426258339
_diffrn_orient_matrix_UB_12      -0.0111979049
_diffrn_orient_matrix_UB_13      0.0467001154
_diffrn_orient_matrix_UB_21      -0.0457904145
_diffrn_orient_matrix_UB_22      -0.0252790149
_diffrn_orient_matrix_UB_23      -0.0445696694
_diffrn_orient_matrix_UB_31      0.0284296773
_diffrn_orient_matrix_UB_32      -0.0577167866
_diffrn_orient_matrix_UB_33      0.0107296622
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14194
_diffrn_reflns_theta_full        30.99
_diffrn_reflns_theta_max         30.99
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.97545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
        (compiled Jun 12 2006,17:01:16)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0572P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                2514
_reflns_number_total             3859
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo800007gsup1.cif
_cod_data_source_block           irm053
_cod_original_sg_symbol_Hall     -p_2ybc
_cod_database_code               4028910