Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)2 on Aminopalladation Stereoselectivity
Claudio Martínez; Yichen Wu; Adam B. Weinstein; Shannon S. Stahl; Guosheng Liu; Kilian Muñiz; Journal of Organic Chemistry 78 (2013) 6309–6315; doi:10.1021/jo400671q

data_4028338
_publ_section_title
;
 Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the
 Influence of PhI(OAc)2 on Aminopalladation Stereoselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6309
_journal_page_last               6315
_journal_paper_doi               10.1021/jo400671q
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   8.7085(16)
_cell_length_b                   12.512(2)
_cell_length_c                   31.644(7)
_cell_measurement_reflns_used    4542
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.59
_cell_measurement_theta_min      2.57
_cell_volume                     3448.0(11)
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR2008
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19074
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         2.57
_diffrn_source                   'rotating anode x-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.9902
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3405
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.281
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.1143
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+15.8617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2260
_refine_ls_wR_factor_ref         0.2346
_reflns_number_gt                2650
_reflns_number_total             3405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400671q_si_002.cif
_cod_data_source_block           cm40c_0m
_cod_original_cell_volume        3447.9(12)
_cod_database_code               4028338