Practical Asymmetric Synthesis of a γ-Secretase Inhibitor Exploiting Substrate-Controlled Intramolecular Nitrile Oxide-Olefin Cycloaddition
Jeremy P. Scott; Steven F. Oliver; Karel M. J. Brands; Sarah E. Brewer; Antony J. Davies; Andrew D. Gibb; David Hands; Stephen P. Keen; Faye J. Sheen; Robert A. Reamer; Robert D. Wilson; Ulf-H. Dolling; Journal of Organic Chemistry 71 (2006) 3086–3092; doi:10.1021/jo060033i

data_4021629
_publ_section_title
;
 Practical Asymmetric Synthesis of a \g-Secretase Inhibitor
 Exploiting Substrate-Controlled Intramolecular
 Nitrile Oxide-Olefin Cycloaddition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3086
_journal_page_last               3092
_journal_paper_doi               10.1021/jo060033i
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C23 H24 F5 N O4 S2'
_chemical_formula_weight         537.55
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   11.4564(4)
_cell_length_b                   11.4564(4)
_cell_length_c                   16.2373(12)
_cell_measurement_temperature    298(2)
_cell_volume                     1845.61(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19548
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.285
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             834
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5014
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.0077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                3929
_reflns_number_total             5014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060033isi20060106_082605.cif
_cod_database_code               4021629