A stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of alpha-aminoacids.
Hoang, Cam Thuy; Alezra, Valérie; Guillot, Régis; Kouklovsky, Cyrille; Organic letters 9 (2007) 2521–2524; doi:10.1021/ol0708020

data_1505419
_publ_section_title
;
 A stereoselective entry into functionalized 1,2-diamines by zinc-mediated
 homologation of alpha-aminoacids.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2521
_journal_page_last               2524
_journal_paper_doi               10.1021/ol0708020
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C12 H22 N2 O3, O0.50'
_chemical_formula_sum            'C12 H22 N2 O3.5'
_chemical_formula_weight         250.32
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 101.286(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.4890(17)
_cell_length_b                   14.7552(14)
_cell_length_c                   14.3559(13)
_cell_measurement_reflns_used    2504
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.51
_cell_volume                     3425.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.789
_diffrn_measured_fraction_theta_max 0.789
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7034
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'X8 Apex Bruker'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            none
_exptl_crystal_density_diffrn    0.971
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.000(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0695
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                1949
_reflns_number_total             3097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0708020si20070405_055114.cif
_cod_data_source_block           181hoang100k
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C12 H22 N2 O3.50'
_cod_database_code               1505419