Unlocking Ylide Reactivity in the Metal-Catalyzed Allylic Substitution Reaction: Stereospecific Construction of Primary Allylic Amines with Aza-Ylides
P. Andrew Evans; Elizabeth A. Clizbe; Journal of the American Chemical Society 131 (2009) 8722–8723; doi:10.1021/ja9041302

data_4104633
_publ_section_title
;
 Unlocking Ylide Reactivity in the Metal-Catalyzed Allylic Substitution
 Reaction: Stereospecific Construction of Primary Allylic Amines with
 Aza-Ylides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8722
_journal_page_last               8723
_journal_paper_doi               10.1021/ja9041302
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C18 H17 N2 +, I -'
_chemical_formula_sum            'C18 H17 I N2'
_chemical_formula_weight         388.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.16(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.287(5)
_cell_length_b                   8.552(2)
_cell_length_c                   11.053(3)
_cell_measurement_reflns_used    912
_cell_measurement_temperature    128(2)
_cell_measurement_theta_max      33.702
_cell_measurement_theta_min      3.803
_cell_volume                     1633.7(8)
_computing_cell_refinement       'SAINT 7.16B (Bruker, 2005)'
_computing_data_collection       'SMART 5.630 (Bruker, 2003)'
_computing_data_reduction        'SAINT 7.16B; XTEL (Local library)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      128(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
'   0.30 degree frames measured for  30.15 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            48095
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Semi-empirical absorption correction via TWINABS 1.05 (Bruker Nonius, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.131
_refine_diff_density_min         -1.300
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc
   [\s^2^(Fo^2^)+6Fo^2^+(0.015Fo^2^)^2^]^-1^
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0755
_reflns_number_gt                2873
_reflns_number_total             4751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9041302_si_001.cif
_cod_data_source_block           05257
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4104633