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_4028911
_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_absolute_configuration syn
_chemical_formula_moiety         'C15 H20 N2 O4'
_chemical_formula_sum            'C15 H20 N2 O4'
_chemical_formula_weight         292.33
_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_date             2006-10-12T20:06:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.224(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2974(4)
_cell_length_b                   7.5545(2)
_cell_length_c                   10.7280(4)
_cell_measurement_reflns_used    3899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.4825
_cell_measurement_theta_min      2.6306
_cell_volume                     736.42(5)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
        (compiled Aug 28 2006,13:05:05)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
        (compiled Aug 28 2006,13:05:05)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
        (compiled Aug 28 2006,13:05:05)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type
;

 Oxford Diffraction Xcalibur diffractometer
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10276
_diffrn_reflns_theta_full        31
_diffrn_reflns_theta_max         31
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.95381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
        (compiled Aug 28 2006,13:05:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                1902
_reflns_number_total             2430
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo800007gsup2.cif
_cod_data_source_block           irm065
_cod_original_sg_symbol_Hall     p_2yb
_cod_database_code               4028911