Palladium-Catalyzed Vinylation of Aminals with Simple Alkenes: A New Strategy To Construct Allylamines
Yinjun Xie; Jianhua Hu; Yanyu Wang; Chungu Xia; Hanmin Huang; Journal of the American Chemical Society 134 (2012) 20613–20616; doi:10.1021/ja310848x

data_4119059
_publ_contact_author_name
;
;
_publ_section_title
;
 Palladium-Catalyzed Vinylation of Aminals with Simple Alkenes: A New
 Strategy To Construct Allylamines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20613
_journal_page_last               20616
_journal_paper_doi               10.1021/ja310848x
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H26 N'
_chemical_formula_sum            'C27 H26 N'
_chemical_formula_weight         364.48
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-22
_audit_creation_method
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  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.668(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1308(5)
_cell_length_b                   33.463(4)
_cell_length_c                   10.2958(7)
_cell_measurement_reflns_used    834
_cell_measurement_temperature    294.32(10)
_cell_measurement_theta_max      72.9557
_cell_measurement_theta_min      4.2909
_cell_volume                     2112.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      294.32(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.7983
_diffrn_measured_fraction_theta_max 0.8118
_diffrn_measurement_details
;
  1 omega   -4.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 61

  2 omega    1.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -83.0000   27.0000 29

  3 omega  -72.00  -46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   57.0000  120.0000 26

  4 omega  -44.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   57.0000  120.0000 42

  5 omega -113.00  -81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000 -120.0000 32

  6 omega  -49.00    2.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   50.0000    0.0000 51

  7 omega -132.00  -72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000 -143.0000  152.0000 60

  8 omega   41.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000  150.0000 29

  9 omega   43.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000   90.0000 51

 10 omega   42.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  150.0000 51

 11 omega  133.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   60.0000 45

 12 omega  103.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  150.0000 29

 13 omega   68.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  150.0000 25

 14 omega  120.00  149.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000  150.0000 29

 15 omega   79.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -120.0000 25

 16 omega  153.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000  150.0000 25

 17 omega   62.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000    0.0000 64

 18 omega   52.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000    0.0000 40

 19 omega   43.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   60.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0130478000
_diffrn_orient_matrix_UB_12      -0.0016705000
_diffrn_orient_matrix_UB_13      -0.1494127000
_diffrn_orient_matrix_UB_21      -0.1209761000
_diffrn_orient_matrix_UB_22      0.0403310000
_diffrn_orient_matrix_UB_23      -0.0018464000
_diffrn_orient_matrix_UB_31      0.2199559000
_diffrn_orient_matrix_UB_32      0.0221104000
_diffrn_orient_matrix_UB_33      -0.0080578000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5783
_diffrn_reflns_theta_full        73.11
_diffrn_reflns_theta_max         73.11
_diffrn_reflns_theta_min         4.29
_diffrn_source                   'SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       0.0061(15)
_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   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         4412
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1782
_refine_ls_R_factor_gt           0.0971
_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^)+(0.1832P)^2^+0.3549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2751
_refine_ls_wR_factor_ref         0.3725
_reflns_number_gt                1974
_reflns_number_total             4412
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310848x_si_003.cif
_cod_data_source_block           xieyj1021
_cod_database_code               4119059
_reflns_odcompleteness_completeness 79.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33