Highly diastereoselective addition of nitromethane anion to chiral alpha-amidoalkylphenyl sulfones. Synthesis of optically active alpha-amino acid derivatives.
Foresti, Elisabetta; Palmieri, Gianni; Petrini, Marino; Profeta, Roberto; Organic & biomolecular chemistry 1 (2003) 4275–4281; doi:10.1039/b309211a

data_7151568
_publ_section_title
;
 Highly diastereoselective addition of nitromethane anion to chiral
 alpha-amidoalkylphenyl sulfones. Synthesis of optically active
 alpha-amino acid derivatives.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4275
_journal_page_last               4281
_journal_paper_doi               10.1039/b309211a
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C17 H25 N O6 S'
_chemical_formula_weight         371.44
_space_group_IT_number           19
_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                   9.9643(4)
_cell_length_b                   11.1330(4)
_cell_length_c                   17.3159(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1920.90(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25018
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9612
_exptl_absorpt_correction_T_min  0.9426
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         5606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0693P)^2^+0.0347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                5339
_reflns_number_total             5606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b309211a.txt
_cod_data_source_block           pet
_cod_database_code               7151568