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_4028912
_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         'C17 H24 N2 O4'
_chemical_formula_sum            'C17 H24 N2 O4'
_chemical_formula_weight         320.38
_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_date             2007-07-06T12:22:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                104.491(4)
_cell_angle_beta                 110.487(4)
_cell_angle_gamma                91.622(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2263(5)
_cell_length_b                   9.6271(5)
_cell_length_c                   10.3118(4)
_cell_measurement_reflns_used    7453
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.5032
_cell_measurement_theta_min      2.5602
_cell_volume                     823.89(8)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.0009
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;

 Oxford Diffraction Xcalibur diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_UB_11      0.0651465602
_diffrn_orient_matrix_UB_12      -0.0183837764
_diffrn_orient_matrix_UB_13      -0.0190757556
_diffrn_orient_matrix_UB_21      0.017696985
_diffrn_orient_matrix_UB_22      0.0729490282
_diffrn_orient_matrix_UB_23      0.0024016777
_diffrn_orient_matrix_UB_31      0.0478297389
_diffrn_orient_matrix_UB_32      0.0148383317
_diffrn_orient_matrix_UB_33      0.0738840954
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12250
_diffrn_reflns_theta_full        30
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.96906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
        (compiled May  8 2007,13:10:02)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1144P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.142
_reflns_number_gt                3559
_reflns_number_total             4787
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo800007gsup3.cif
_cod_data_source_block           irm209
_cod_original_sg_symbol_Hall     -p_1
_cod_database_code               4028912