Direct Asymmetric Michael Addition to Nitroalkenes: Vinylogous Nucleophilicity under Dinuclear Zinc Catalysis
Barry M. Trost; Julien Hitce; Journal of the American Chemical Society 131 (2009) 4572–4573; doi:10.1021/ja809723u

data_4104128
_publ_contact_author_address     'Dept. of Chemistry, Stanford University'
_publ_contact_author_email       hitce@stanford.edu
_publ_contact_author_name        'Julien Hitce'
_publ_contact_author_phone       '650 265 8982'
_publ_section_title
;
 Direct Asymmetric Michael Addition to Nitroalkenes: Vinylogous
 Nucleophilicity under Dinuclear Zinc Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4572
_journal_page_last               4573
_journal_paper_doi               10.1021/ja809723u
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H10 Cl N O4'
_chemical_formula_sum            'C12 H10 Cl N O4'
_chemical_formula_weight         267.66
_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                   6.2981(14)
_cell_length_b                   7.5510(16)
_cell_length_c                   25.114(6)
_cell_measurement_reflns_used    6045
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.82
_cell_volume                     1194.3(5)
_computing_cell_refinement       'Bruker SAINT v7.34A'
_computing_data_collection       'Bruker APEX-II v2.1-4'
_computing_data_reduction        'Bruker SAINT v7.34A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       \w/2\q-scans
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13510
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_correction_T_min  0.9528
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.1645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0706
_reflns_number_gt                2758
_reflns_number_total             2958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809723u_si_002.cif
_cod_data_source_block           stanu022
_cod_database_code               4104128