Phosphine-Catalyzed [4 + 1] Annulation between α,β-Unsaturated Imines and Allylic Carbonates: Synthesis of 2-Pyrrolines
Junjun Tian; Rong Zhou; Haiyun Sun; Haibin Song; Zhengjie He; Journal of Organic Chemistry 76 (2011) 2374–2378; doi:10.1021/jo200164v

data_4026179
_publ_section_title
;
 Phosphine-Catalyzed [4 + 1] Annulation between \a,\b-Unsaturated Imines
 and Allylic Carbonates: Synthesis of 2-Pyrrolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2374
_journal_page_last               2378
_journal_paper_doi               10.1021/jo200164v
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C28 H27 N O4 S'
_chemical_formula_weight         473.57
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.40(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7073(15)
_cell_length_b                   12.316(3)
_cell_length_c                   25.270(5)
_cell_measurement_reflns_used    5395
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.894
_cell_measurement_theta_min      1.843
_cell_volume                     2373.0(9)
_computing_cell_refinement       crystalclear
_computing_data_collection       'crystalclear(Rigaku/MSC Inc., 2005)'
_computing_data_reduction        crystalclear
_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      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'rigaku saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15619
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.055(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   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0985P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1798
_reflns_number_gt                2211
_reflns_number_total             4181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200164v_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2373.0(8)
_cod_database_code               4026179