Enantioselective synthesis of 4-aminopyrrolidine-2,4-dicarboxylate derivatives via Ag-catalyzed cycloaddition of azomethine ylides with alkylidene azlactones
Maria Gonzalez-Esguevillas; Javier Adrio; Juan C. Carretero; Chem.Commun. 49 (2013) 4649–; doi:10.1039/c3cc41663a

data_7109274
_publ_section_title
;
 Enantioselective synthesis of 4-aminopyrrolidine-2,4-dicarboxylate
 derivatives via Ag-catalyzed cycloaddition of azomethine ylides with
 alkylidene azlactones
;
_journal_name_full               Chem.Commun.
_journal_page_first              4649
_journal_paper_doi               10.1039/c3cc41663a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C27 H25 Br N2 O5'
_chemical_formula_weight         537.40
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   14.0226(2)
_cell_length_b                   14.0226(2)
_cell_length_c                   22.0805(8)
_cell_measurement_reflns_used    5784
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      65.83
_cell_measurement_theta_min      3.64
_cell_volume                     3760.08(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20231
_diffrn_reflns_theta_full        67.18
_diffrn_reflns_theta_max         67.18
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    2.571
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0400P)^2^+0.6471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                3333
_reflns_number_total             3617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41663a.txt
_cod_data_source_block           170fin
_cod_original_cell_volume        3760.07(16)
_cod_original_sg_symbol_H-M      P6(5)
_cod_database_code               7109274