Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes
Daniel Best; Szymon Kujawa; Hon Wai Lam; Journal of the American Chemical Society 134 (2012) 18193–18196; doi:10.1021/ja3083494

data_4118867
_publ_section_title
;
 Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of
 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18193
_journal_page_last               18196
_journal_paper_doi               10.1021/ja3083494
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N3 O3'
_chemical_formula_sum            'C18 H19 N3 O3'
_chemical_formula_weight         325.36
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.91759(3)
_cell_length_b                   11.50337(5)
_cell_length_c                   24.58172(11)
_cell_measurement_reflns_used    77697
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.2643
_cell_measurement_theta_min      3.5931
_cell_volume                     1673.332(13)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2011)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3147
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0064
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            95457
_diffrn_reflns_theta_full        76.42
_diffrn_reflns_theta_max         76.42
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.8765
_exptl_absorpt_correction_T_min  0.7594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21d (release 25-05-2012 CrysAlis171 .NET)
(compiled May 25 2012,16:20:25)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1456 Friedel pairs '
_refine_ls_abs_structure_Flack   0.02(14)
_refine_ls_extinction_coef       0.0034(4)
_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   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0245
_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^)+(0.0379P)^2^+0.2725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                3502
_reflns_number_total             3508
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja3083494_si_003.cif
_cod_data_source_block           hl2021
_cod_original_cell_volume        1673.333(14)
_cod_database_code               4118867