Synthesis of a Chiral C2-Symmetric Sterically Hindered Pyrrolidine Nitroxide Radical via Combined Iterative Nucleophilic Additions and Intramolecular 1,3-Dipolar Cycloadditions to Cyclic Nitrones
Denis A. Morozov; Igor A. Kirilyuk; Denis A. Komarov; Andrea Goti; Irina Yu. Bagryanskaya; Natalia V. Kuratieva; Igor A. Grigor'ev; Journal of Organic Chemistry 77 (2012) 10688–10698; doi:10.1021/jo3019158

data_4027759
_publ_contact_author_address
;Institute of Organic Chemistry,
SB Russian Academy of Sciences,
Akad. Lavrentiev prospekt 9,
Novosibirsk 90,
630090 Russia
;
_publ_contact_author_email       m_falcon@nioch.nsc.ru
_publ_contact_author_fax         7(383)3309752
_publ_contact_author_name        'Denis A. Morozov'
_publ_contact_author_phone       7(383)3307387
_publ_section_title
;
 Synthesis of a Chiral C2-Symmetric Sterically Hindered Pyrrolidine
 Nitroxide Radical via Combined Iterative Nucleophilic Additions and
 Intramolecular 1,3-Dipolar Cycloadditions to Cyclic Nitrones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10688
_journal_page_last               10698
_journal_paper_doi               10.1021/jo3019158
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H38.14 N O3'
_chemical_formula_sum            'C22 H38.14 N O3'
_chemical_formula_weight         364.67
_chemical_melting_point          333
_chemical_name_systematic
; 
 1,2-Di-tert-butoxy-3-
 (pent-4-enyl)octahydrocyclopenta[c]pyrrolo[1,2-b]isoxazolidine  
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9167(9)
_cell_length_b                   11.6882(19)
_cell_length_c                   20.8027(15)
_cell_measurement_reflns_used    9771
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.48
_cell_volume                     2168.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(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         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34037
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       plate
_exptl_crystal_F_000             805
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         5245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0648P)^2^+0.2265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                5004
_reflns_number_total             5245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3019158_si_002.cif
_cod_data_source_block           d222_0m
_cod_database_code               4027759