Enantioselective Synthesis of Homoallylic Amines through Reactions of (Pinacolato)allylborons with Aryl-, Heteroaryl-, Alkyl-, or Alkene-Substituted Aldimines Catalyzed by Chiral C1-Symmetric NHC-Cu Complexes
Erika M. Vieira; Marc L. Snapper; Amir H. Hoveyda; Journal of the American Chemical Society 133 (2011) 3332–3335; doi:10.1021/ja200311n

data_4105763
_publ_section_title
;
 Enantioselective Synthesis of Homoallylic Amines through Reactions of
 (Pinacolato)allylborons with Aryl-, Heteroaryl-, Alkyl-, or
 Alkene-Substituted Aldimines Catalyzed by Chiral C1-Symmetric NHC-Cu
 Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3332
_journal_page_last               3335
_journal_paper_doi               10.1021/ja200311n
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 N O P'
_chemical_formula_sum            'C22 H22 N O P'
_chemical_formula_weight         347.38
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.297(3)
_cell_angle_beta                 79.005(3)
_cell_angle_gamma                89.123(3)
_cell_formula_units_Z            4
_cell_length_a                   8.6853(5)
_cell_length_b                   11.3946(6)
_cell_length_c                   20.2971(11)
_cell_measurement_reflns_used    8099
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.78
_cell_measurement_theta_min      2.41
_cell_volume                     1896.84(18)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w 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  0.0737
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            57723
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.9729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(8)
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     910
_refine_ls_number_reflns         16102
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0879P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                11274
_reflns_number_total             16102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja200311n_si_004.cif
_cod_data_source_block           C22H22NOP
_cod_original_cell_volume        1896.85(18)
_cod_database_code               4105763