Asymmetric Synthesis of β-Nitro Ketones via Michael Addition of Lithiated α-Amino Nitriles to Nitroalkenes
Dieter Enders; Dominik Förster; Gerhard Raabe; Jan W. Bats; Journal of Organic Chemistry 73 (2008) 9641–9646; doi:10.1021/jo8017318

data_4023935
_publ_section_title
;
 Asymmetric Synthesis of \b-Nitro Ketones via Michael Addition
 of Lithiated \a-Amino Nitriles to Nitroalkenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9641
_journal_page_last               9646
_journal_paper_doi               10.1021/jo8017318
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H17 N O5'
_chemical_formula_weight         279.29
_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'
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4
_cell_length_a                   7.9300(3)
_cell_length_b                   9.812(4)
_cell_length_c                   17.277(9)
_cell_measurement_temperature    150
_cell_volume                     1344.3(9)
_computing_data_reduction        'xtal DIFDAT SORTRF ADDREF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    xtal
_diffrn_ambient_temperature      293
_diffrn_measurement_device_type  CAD4
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  .063
_diffrn_reflns_av_sigmaI/netI    .069
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3100
_diffrn_reflns_reduction_process 'perpendicular monochr Lp'
_diffrn_reflns_theta_max         72.76
_diffrn_reflns_theta_min         5.12
_exptl_absorpt_coefficient_mu    .882
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_F_000             592
_refine_diff_density_max         .53
_refine_diff_density_min         -.675
_refine_ls_extinction_coef       .00000
_refine_ls_goodness_of_fit_all   1.544
_refine_ls_goodness_of_fit_ref   1.653
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .082
_refine_ls_R_factor_gt           .057
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .065
_refine_ls_wR_factor_ref         .063
_reflns_d_resolution_high        .807
_reflns_d_resolution_low         8.639
_reflns_Friedel_coverage         .729
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                2194
_reflns_number_total             2635
_reflns_threshold_expression     'I    >  2.00 sig(I   )'
_cod_data_source_file            jo8017318_si_002.cif
_cod_data_source_block           gr0561
_cod_original_sg_symbol_Hall     p_2ac_2ab
_cod_original_formula_sum        'C14 H17 N1 O5'
_cod_database_code               4023935