Highly Diastereo- and Enantioselective Pd-Catalyzed Cyclopropanation of Acyclic Amides with Substituted Allyl Carbonates
Wei Liu; Di Chen; Xia-Zhen Zhu; Xiao-Long Wan; Xue-Long Hou; Journal of the American Chemical Society 131 (2009) 8734–8735; doi:10.1021/ja902410w

data_4104602
_publ_section_title
;
 Highly Diastereo- and Enantioselective Pd-Catalyzed Cyclopropanation of
 Acyclic Amides with Substituted Allyl Carbonates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8734
_journal_page_last               8735
_journal_paper_doi               10.1021/ja902410w
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H26 Br N O'
_chemical_formula_weight         448.39
_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   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            4
_cell_length_a                   9.2297(14)
_cell_length_b                   10.7223(17)
_cell_length_c                   22.792(4)
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.313
_cell_measurement_theta_min      4.761
_cell_volume                     2255.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0815
_diffrn_reflns_av_sigmaI/netI    0.0978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12323
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    1.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75134
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.311
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.026(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc 
 [0.00000+1.00000exp(2.00(sin\q/\l)^2^)]/ 
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0281P)^2^+0.0000sin\q/\l] 
 where P = 0.33333Fo^2^ + 0.66667Fc^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                2340
_reflns_number_total             4432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja902410w_si_002.cif
_cod_data_source_block           cd2979
_cod_database_code               4104602