Nucleophilic Phosphine-Catalyzed Intramolecular Michael Reactions of N-Allylic Substituted α-Amino Nitriles: Construction of Functionalized Pyrrolidine Rings via 5-endo-trig Cyclizations.
En, Da; Zou, Gong-Feng; Guo, Yuan; Liao, Wei-Wei; The Journal of organic chemistry 79 (2014) 4456–4462; doi:10.1021/jo500418s

data_4029426
_publ_section_title
;
 Nucleophilic Phosphine-Catalyzed Intramolecular Michael Reactions of
 N-Allylic Substituted \a-Amino Nitriles: Construction of Functionalized
 Pyrrolidine Rings via 5-endo-trig Cyclizations.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4456
_journal_page_last               4462
_journal_paper_doi               10.1021/jo500418s
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 106.45(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.120(2)
_cell_length_b                   10.669(2)
_cell_length_c                   16.642(3)
_cell_measurement_reflns_used    12976
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.19
_cell_volume                     1723.3(6)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       '\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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16369
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_correction_T_min  0.9504
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0803P)^2^+0.0493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                3049
_reflns_number_total             3926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500418s_si_001.cif
_cod_data_source_block           ed001
_cod_depositor_comments          'Adding full bibliography for 4029426.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4029426