Enantioselective Palladium-Catalyzed Diamination of Alkenes Using N-Fluorobenzenesulfonimide
Erica L. Ingalls; Paul A. Sibbald; Werner Kaminsky; Forrest E. Michael; Journal of the American Chemical Society 135 (2013) 8854–8856; doi:10.1021/ja4043406

data_4119954
_publ_contact_author_address
;
Department of Chemistry
University of Washington
Seattle
Washington, 98195, USA
;
_publ_contact_author_email       kaminsky@chem.washington.edu
_publ_contact_author_fax         00(206)6858665
_publ_contact_author_name        'Werner Kaminsky'
_publ_contact_author_phone       00(206)5437585
_publ_section_title
;
 Enantioselective Palladium-Catalyzed Diamination of Alkenes Using
 N-Fluorobenzenesulfonimide
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8854
_journal_page_last               8856
_journal_paper_doi               10.1021/ja4043406
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H30 N3 O2 Pd, C2 H F3 O2, C2 F3 O2 '
_chemical_formula_sum            'C31 H31 F6 N3 O6 Pd'
_chemical_formula_weight         761.99
_chemical_name_common            ingalls001
_chemical_name_systematic
;
 ingalls001
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-07-16T10:13:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7794(3)
_cell_length_b                   12.2839(5)
_cell_length_c                   38.5200(16)
_cell_measurement_reflns_used    386
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      3
_cell_volume                     3207.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            29762
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_correction_T_min  0.8264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       prism
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.917
_refine_diff_density_min         -1.851
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         7939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+4.6894P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                6926
_reflns_number_total             7939
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja4043406_si_003.cif
_cod_data_source_block           ingalls001_0m
_cod_database_code               4119954