Nucleophilic Ring-Opening of Epoxide and Aziridine Acetates for the Stereodivergent Synthesis of β-Hydroxy and β-Amino γ-Lactams
Tula B. Bisol; Adailton J. Bortoluzzi; Marcus M. Sá; Journal of Organic Chemistry 76 (2011) 948–962; doi:10.1021/jo102267h

data_4026036
_publ_contact_author_address
;
    Depto. de Qu\'imica - UFSC
    88040 - 900 Florian\'opolis, SC
    Brazil
;
_publ_contact_author_email       msa@qmc.ufsc.br
_publ_contact_author_fax         55(48)37216888
_publ_contact_author_name        'Marcus M. S\'a'
_publ_contact_author_phone       55(48)37216844
_publ_section_title
;
 Nucleophilic Ring-Opening of Epoxide and Aziridine Acetates for the
 Stereodivergent Synthesis of \b-Hydroxy and \b-Amino \g-Lactams
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              948
_journal_page_last               962
_journal_paper_doi               10.1021/jo102267h
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C6 H11 N O2'
_chemical_formula_weight         129.16
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 and manual editing'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.511(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5881(7)
_cell_length_b                   14.0647(9)
_cell_length_c                   10.4202(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.62
_cell_measurement_theta_min      6.58
_cell_volume                     668.08(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1514
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0491P)^2^+0.1820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                1178
_reflns_number_total             1443
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo102267h_si_004.cif
_cod_data_source_block           10b_anti
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026036