Three-component organocascade kinetic resolution of racemic nitroallylic acetates via sequential iminium/enamine asymmetric catalysis.
Roy, Suparna; Chen, Kwunmin; Organic letters 14 (2012) 2496–2499; doi:10.1021/ol300783e

data_1507679
_publ_section_title
;
 Three-component organocascade kinetic resolution of racemic nitroallylic
 acetates via sequential iminium/enamine asymmetric catalysis.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2496
_journal_page_last               2499
_journal_paper_doi               10.1021/ol300783e
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H23 Br N2 O6'
_chemical_formula_sum            'C24 H23 Br N2 O6'
_chemical_formula_weight         515.35
_chemical_name_systematic
;
Ethyl 6-(5-bromo-1H-indol-3-yl)-5-formyl-4-(3-methoxyphenyl)-3-nitrohex-(2E)-enoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   9.3506(3)
_cell_length_b                   10.3827(4)
_cell_length_c                   23.1640(8)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2248.86(14)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7448
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_T_max  0.8960
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.710
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.710
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0380P)^2^+3.2709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                2695
_reflns_number_total             3585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300783e_si_001.cif
_cod_data_source_block           a13318
_cod_depositor_comments          'Adding full bibliography for 1507679.cif.'
_cod_database_code               1507679