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_4023934
_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_moiety         'C27 H34 Br N3 O4'
_chemical_formula_sum            'C27 H34 Br N3 O4'
_chemical_formula_weight         544.48
_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                   9.1160(14)
_cell_length_b                   9.3500(10)
_cell_length_c                   31.497(5)
_cell_measurement_reflns_used    209
_cell_measurement_temperature    162(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     2684.6(7)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      162(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  SIEMENS_SMART_CCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            44787
_diffrn_reflns_theta_full        30.91
_diffrn_reflns_theta_max         30.91
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         390
_exptl_absorpt_coefficient_mu    1.568
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   ' SHELXTL (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(6)
_refine_ls_extinction_coef       0.0035(4)
_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   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         7839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.04P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                5400
_reflns_number_total             7839
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo8017318_si_001.cif
_cod_data_source_block           df129
_cod_database_code               4023934