Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines
Christopher W. Bond; Alexander J. Cresswell; Stephen G. Davies; Ai M. Fletcher; Wataru Kurosawa; James A. Lee; Paul M. Roberts; Angela J. Russell; Andrew D. Smith; James E. Thomson; Journal of Organic Chemistry 74 (2009) 6735–6748; doi:10.1021/jo9012783

data_4024823
_publ_contact_author_address
;Department of Chemistry
Chemistry Research laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_name        'Stephen G. davies'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6735
_journal_page_last               6748
_journal_paper_doi               10.1021/jo9012783
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C21 H27 N1 O2'
_chemical_formula_sum            'C21 H27 N O2'
_chemical_formula_weight         325.45
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             05-04-29
_audit_creation_method           CRYSTALS_ver_12.50
_cell_angle_alpha                100.7822(6)
_cell_angle_beta                 93.3074(7)
_cell_angle_gamma                109.7640(10)
_cell_formula_units_Z            4
_cell_length_a                   9.80800(10)
_cell_length_b                   12.7341(2)
_cell_length_c                   15.9205(3)
_cell_measurement_reflns_used    7701
_cell_measurement_temperature    123
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1822.44(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15239
_diffrn_reflns_theta_full        26.598
_diffrn_reflns_theta_max         27.421
_diffrn_reflns_theta_min         5.106
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         8195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.000255
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 p=(max(Fo^2^,0) + 2Fc^2^)/3 
 Method = SHELXL 97 (Sheldrick, 1997) 
 w=1/[sigma^2^(F^2^) + 0.04 + 0.49p] 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1140
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1140
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                8195
_reflns_number_total             8196
_reflns_threshold_expression     I>-10.00u(I)
_oxford_diffrn_Wilson_B_factor   3.03
_oxford_diffrn_Wilson_scale      1.53
_oxford_refine_ls_scale          0.7652(16)
_oxford_structure_analysis_title '4260951 pr73'
_cod_data_source_file            jo9012783_si_018.cif
_cod_data_source_block           CRYSTALS_cif
_cod_original_formula_sum        'C21 H27 N1 O2'
_cod_database_code               4024823