Dynamic Kinetic Asymmetric Ring-Opening/Reductive Amination Sequence of Racemic Nitroepoxides with Chiral Amines: Enantioselective Synthesis of Chiral Vicinal Diamines
Juan Agut; Andreu Vidal; Santiago Rodríguez; Florenci V. González; Journal of Organic Chemistry 78 (2013) 5717–5722; doi:10.1021/jo400501k

data_4028280
_publ_section_title
;
 Dynamic Kinetic Asymmetric Ring-Opening/Reductive Amination Sequence of
 Racemic Nitroepoxides with Chiral Amines: Enantioselective Synthesis of
 Chiral Vicinal Diamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5717
_journal_page_last               5722
_journal_paper_doi               10.1021/jo400501k
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C25 H30 Cl2 N2'
_chemical_formula_weight         429.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 116.253(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.22335(20)
_cell_length_b                   14.6654(3)
_cell_length_c                   9.7778(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1186.16(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11697
_diffrn_reflns_theta_full        72.78
_diffrn_reflns_theta_max         72.78
_diffrn_reflns_theta_min         5.04
_exptl_absorpt_coefficient_mu    2.545
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             456
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0555P)^2^+0.1808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                3821
_reflns_number_total             4125
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400501k_si_001.cif
_cod_data_source_block           str1339
_cod_original_cell_volume        1186.17(4)
_cod_database_code               4028280