Novel Diastereoselective Synthesis of Bicyclic β-Lactams through Radical Cyclization and Their Reduction toward 2-(1-Alkoxy-2-hydroxyethyl)piperidines and 2-(1-Alkoxy-2-hydroxyethyl)azepanes
Erika Leemans; Matthias D'hooghe; Yves Dejaegher; Karl W. Törnroos; Norbert De Kimpe; Journal of Organic Chemistry 73 (2008) 1422–1428; doi:10.1021/jo702263p

data_4023272
_publ_section_title
;
 Novel Diastereoselective Synthesis of Bicyclic \b-Lactams
 through Radical Cyclization and Their Reduction toward
 2-(1-Alkoxy-2-hydroxyethyl)piperidines and
 2-(1-Alkoxy-2-hydroxyethyl)azepanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1422
_journal_page_last               1428
_journal_paper_doi               10.1021/jo702263p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C16 H21 N O2'
_chemical_formula_sum            'C16 H21 N O2'
_chemical_formula_weight         259.34
_chemical_name_systematic
; 
3,5,5-trimethyl-7-phenoxy-1-azabicyclo[4.2.0]octan-8-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.3350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9037(3)
_cell_length_b                   9.5546(4)
_cell_length_c                   16.7734(6)
_cell_measurement_reflns_used    18160
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      24.09
_cell_measurement_theta_min      2.30
_cell_volume                     1418.22(9)
_computing_cell_refinement
;
Bruker (2001). SAINT, version 6.02a, Bruker AXS Inc., Madison, 
Wisconsin, USA.
;
_computing_data_collection
;
Bruker (1999). SMART, version 5.059, Bruker AXS Inc., Madison, 
Wisconsin, USA.
;
_computing_data_reduction
;
Bruker (2001). SAINT, version 6.02a, Bruker AXS Inc., Madison, 
Wisconsin, USA.
;
_computing_molecular_graphics
;
Brandenburg, K. (2005). 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. (1997). SHELXS97 and SHELXL97. University of 
G\"ottingen, Germany.
;
_computing_structure_solution
;     
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of 
G\"ottingen, Germany. 
;
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean '48 \um'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-AXS SMART 2K CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0100
_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       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21600
_diffrn_reflns_theta_full        29.09
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  28h
_diffrn_standards_number         537
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9562
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Bruker AXS (2003). SHELXTL. Version 6.14. 
Bruker AXS Inc., Madison, Wisconsin, USA. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0504P)^2^+0.3412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                3499
_reflns_number_total             3790
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo702263p-File001.cif
_cod_data_source_block           Compound6b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023272