Chiral Iminoesters Derived fromd-Glyceraldehyde in [3 + 2] Cycloaddition Reactions. Asymmetric Synthesis of a Key Intermediate in the Synthesis of Neuramidinase Inhibitors
José A. Gálvez; María D. Díaz-de-Villegas; Miriam Alías; Ramón Badorrey; Journal of Organic Chemistry 78 (2013) 11404–11413; doi:10.1021/jo401967a

data_4028758
_publ_section_title
;
 Chiral Iminoesters Derived fromd-Glyceraldehyde in [3 + 2] Cycloaddition
 Reactions. Asymmetric Synthesis of a Key Intermediate in the Synthesis of
 Neuramidinase Inhibitors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11404
_journal_page_last               11413
_journal_paper_doi               10.1021/jo401967a
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H29 N O8 S'
_chemical_formula_sum            'C21 H29 N O8 S'
_chemical_formula_weight         455.51
_chemical_name_systematic
; 
(2R,4R,5S)-4-ethyl 2-methyl 5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]
-1-tosylpyrrolidine-2,4-dicarboxylate 
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.342(17)
_cell_angle_beta                 77.216(14)
_cell_angle_gamma                87.954(15)
_cell_formula_units_Z            2
_cell_length_a                   8.2700(12)
_cell_length_b                   9.0465(19)
_cell_length_c                   16.281(3)
_cell_measurement_reflns_used    683
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7860
_cell_measurement_theta_min      3.0717
_cell_volume                     1179.8(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.856
_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  0.0580
_diffrn_reflns_av_sigmaI/netI    0.1915
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8762
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.85
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       prims
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         6795
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.2437
_refine_ls_R_factor_gt           0.0978
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1188P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2320
_refine_ls_wR_factor_ref         0.3064
_reflns_number_gt                2232
_reflns_number_total             6795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401967a_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4028758