Stereoselective Synthesis of Chiral 4-(1-Chloroalkyl)-β-Lactams Starting from Amino Acids and Their Transformation into Functionalized Chiral Azetidines and Pyrrolidines
Stijn Dekeukeleire; Matthias D'hooghe; Karl Wilhelm Törnroos; Norbert De Kimpe; Journal of Organic Chemistry 75 (2010) 5934–5940; doi:10.1021/jo101220q

data_4025645
_publ_contact_author_address
;
       Department of Chemistry,
       University of Bergen,
       Allegaten 41,
       N-5007 Bergen,
       Norway.

;
_publ_contact_author_email       karl.tornroos@kj.uib.no
_publ_contact_author_fax         '+47 55 58 3552'
_publ_contact_author_name
;
       Prof. Karl Wilhelm T\"ornroos
;
_publ_contact_author_phone       '+47 55 58 9490'
_publ_section_title
;
 Stereoselective Synthesis of Chiral 4-(1-Chloroalkyl)-\b-Lactams Starting
 from Amino Acids and Their Transformation into Functionalized Chiral
 Azetidines and Pyrrolidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5934
_journal_page_last               5940
_journal_paper_doi               10.1021/jo101220q
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H28 Cl N O2'
_chemical_formula_sum            'C24 H28 Cl N O2'
_chemical_formula_weight         397.92
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 95.769(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.5869(12)
_cell_length_b                   5.4737(3)
_cell_length_c                   14.5005(7)
_cell_measurement_reflns_used    14696
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      60.026
_cell_measurement_theta_min      5.648
_cell_volume                     2099.55(18)
_computing_cell_refinement
;
Bruker (2008). SAINT, version 7.56A, Bruker AXS Inc., Madison, 
Wisconsin, USA.
;
_computing_data_collection
;
Bruker (2008). APEX2, version 5.054, Bruker AXS Inc., Madison, 
Wisconsin, USA.
;
_computing_data_reduction
;
Bruker (2008). SAINT, version 7.56A, Bruker AXS Inc., Madison, 
Wisconsin, USA.
;
_computing_molecular_graphics
;
Brandenburg, K. (2007). DIAMOND. Version 3.1. Crystal Impact GbR, Bonn, 
Germany.
;
_computing_publication_material
;
Bruker AXS (2003). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, 
Wisconsin, USA.
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008). Acta Crystallographica, A64, 112-122.
;
_computing_structure_solution
;     
Sheldrick, G. M. (2008). Acta Crystallographica, A64, 112-122.
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6046
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.8846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS version 2008/1, G.M Sheldrick, University of 
G\"ttingen, Germany, 2008.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         6046
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0556P)^2^+0.3288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                5940
_reflns_number_total             6046
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo101220q_si_002.cif
_cod_data_source_block           Compound3a
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4025645