Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Allylation of Nitroalkanes with Monosubstituted Allylic Substrates
Xiao-Fei Yang; Wei-Hua Yu; Chang-Hua Ding; Qiu-Ping Ding; Shi-Li Wan; Xue-Long Hou; Li-Xin Dai; Pin-Jie Wang; Journal of Organic Chemistry 78 (2013) 6503–6509; doi:10.1021/jo400663d

data_4028392
_publ_section_title
;
 Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Allylation
 of Nitroalkanes with Monosubstituted Allylic Substrates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6503
_journal_page_last               6509
_journal_paper_doi               10.1021/jo400663d
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H24 Br N O2'
_chemical_formula_weight         354.28
_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                 110.278(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0028(9)
_cell_length_b                   22.187(2)
_cell_length_c                   9.7931(10)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.213
_cell_measurement_theta_min      4.824
_cell_volume                     1834.9(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0733
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11165
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    2.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60263
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(11)
_refine_ls_extinction_coef       0.0042(7)
_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   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0518P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                3201
_reflns_number_total             5494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400663d_si_002.cif
_cod_data_source_block           cd212714
_cod_database_code               4028392