Enantioselective Synthesis of α-Heteroarylpyrrolidines by Copper-Catalyzed 1,3-Dipolar Cycloaddition of α-Silylimines.
Pascual-Escudero, Ana; González-Esguevillas, María; Padilla, Silvia; Adrio, Javier; Carretero, Juan C; Organic letters 16 (2014) 2228–2231; doi:10.1021/ol5007373

data_1514221
_publ_section_title
;
 Enantioselective Synthesis of \a-Heteroarylpyrrolidines by
 Copper-Catalyzed 1,3-Dipolar Cycloaddition of \a-Silylimines.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2228
_journal_page_last               2231
_journal_paper_doi               10.1021/ol5007373
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C17 H14 Br N3 O2'
_chemical_formula_weight         372.22
_chemical_name_common            APE2
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.114(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0087(4)
_cell_length_b                   17.4567(9)
_cell_length_c                   15.2518(12)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      18.6913
_cell_measurement_theta_min      2.9153
_cell_volume                     1599.49(18)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0844
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14467
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.331
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5540
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0839P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1830
_reflns_number_gt                3015
_reflns_number_total             5540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5007373_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514221.cif.
;
_cod_database_code               1514221