Stereoselective Synthesis of Azetidines and Pyrrolidines from N-tert-Butylsulfonyl(2-aminoalkyl)oxiranes
Mohamed Medjahdi; José C. González-Gómez; Francisco Foubelo; Miguel Yus; Journal of Organic Chemistry 74 (2009) 7859–7865; doi:10.1021/jo9016666

data_4024925
_publ_section_title
;
Stereoselective Synthesis of Azetidines and Pyrrolidines
from N-tert-Butylsulfonyl(2-aminoalkyl)oxiranes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7859
_journal_page_last               7865
_journal_paper_doi               10.1021/jo9016666
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H25 N O3 S'
_chemical_formula_sum            'C16 H25 N O3 S'
_chemical_formula_weight         311.43
_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                 102.266(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.613(3)
_cell_length_b                   5.8224(16)
_cell_length_c                   12.483(4)
_cell_measurement_reflns_used    452
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      16.5
_cell_measurement_theta_min      2.7
_cell_volume                     824.8(4)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics
;
SHELXTL  Rel. 6.12/V (Sheldrick, Acta Cryst. 2008, A64, 112-122)
;
_computing_publication_material
;
SHELX-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122)' 
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122) 
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122)
;
_diffrn_ambient_temperature      294(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_av_sigmaI/netI    0.1383
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6895
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(17)
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1695
_reflns_number_gt                1637
_reflns_number_total             2877
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo9016666_si_002.cif
_cod_data_source_block           x
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024925