Stereoselective iodocyclization of (S)-allylalanine derivatives: gamma-lactone vs cyclic carbamate formation.
Pattarozzi, Mariella; Zonta, Cristiano; Broxterman, Quirinus B.; Kaptein, Bernard; De Zorzi, Rita; Randaccio, Lucio; Scrimin, Paolo; Licini, Giulia; Organic letters 9 (2007) 2365–2368; doi:10.1021/ol070764k

data_1505414
_publ_section_title
;
 Stereoselective iodocyclization of (S)-allylalanine derivatives:
 gamma-lactone vs cyclic carbamate formation.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2365
_journal_page_last               2368
_journal_paper_doi               10.1021/ol070764k
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_sum            'C14 H16 I N O4'
_chemical_formula_weight         389.18
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_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_date             2007-02-02T12:09:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.725
_cell_length_b                   13.858
_cell_length_c                   16.061
_cell_measurement_temperature    293(2)
_cell_volume                     1496.806
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5037
_diffrn_reflns_theta_full        30.63
_diffrn_reflns_theta_max         30.63
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    2.152
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         1.322
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.169
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       0.033(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   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+0.4431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1534
_reflns_number_gt                3704
_reflns_number_total             4577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070764ksi20070329_050747.cif
_cod_data_source_block           carbammato
_cod_original_cell_volume        1496.7
_cod_database_code               1505414