Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF4.OEt2: Application to the Asymmetric Synthesis of (S,S)-3-Deoxy-3-fluorosafingol
Alexander J. Cresswell; Stephen G. Davies; James A. Lee; Melloney J. Morris; Paul M. Roberts; James E. Thomson; Journal of Organic Chemistry 76 (2011) 4617–4627; doi:10.1021/jo200517w

data_4026374
_publ_contact_author_address
;Department of Chemistry
Chemistry Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
U.K.
;
_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
;
 Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF4.OEt2:
 Application to the Asymmetric Synthesis of (S,S)-3-Deoxy-3-fluorosafingol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4617
_journal_page_last               4627
_journal_paper_doi               10.1021/jo200517w
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H38 F1 N1 O1'
_chemical_formula_sum            'C18 H38 F N O'
_chemical_formula_weight         303.50
_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
_audit_creation_date             11-01-26
_audit_creation_method           CRYSTALS_ver_14.06
_cell_angle_alpha                90
_cell_angle_beta                 90.9711(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.73792(11)
_cell_length_b                   7.6761(2)
_cell_length_c                   42.7479(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1882.55(7)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3777
_diffrn_reflns_theta_full        75.445
_diffrn_reflns_theta_max         76.984
_diffrn_reflns_theta_min         3.102
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.37
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9582
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3581
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0728
_refine_ls_shift/su_max          0.0004953
_refine_ls_shift/su_mean         0.0000534
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 11.2 3.46 6.59 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0805
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0788
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -9
_reflns_limit_l_max              53
_reflns_limit_l_min              0
_reflns_number_gt                3646
_reflns_number_total             3777
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.44
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0723
_oxford_refine_ls_scale          5.790(15)
_oxford_reflns_number_all        3743
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            jo200517w_si_007.cif
_cod_data_source_block           1
_cod_original_cell_volume        1882.56(7)
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_original_formula_sum        'C18 H38 F1 N1 O1'
_cod_database_code               4026374