Cycloaddition of Alkynyl Ketones with N-Tosylimines Catalyzed by Bu~3~P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines
Ling-Guo Meng; Peijie Cai; Qingxiang Guo; Song Xue; Journal of Organic Chemistry 73 (2008) 8491–8496; doi:10.1021/jo801687v

data_4023824
_publ_section_title
;
 Cycloaddition of Alkynyl Ketones with N-Tosylimines
 Catalyzed by Bu~3~P and DMAP: Synthesis of Highly Functionalized
 Pyrrolidines and Azetidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8491
_journal_page_last               8496
_journal_paper_doi               10.1021/jo801687v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C26 H23 Br N2 O5 S'
_chemical_formula_weight         555.43
_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                90.000(5)
_cell_angle_beta                 106.678(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   13.117(5)
_cell_length_b                   18.601(5)
_cell_length_c                   11.063(5)
_cell_measurement_reflns_used    4360
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      63.1397
_cell_measurement_theta_min      2.3738
_cell_volume                     2585.7(17)
_computing_cell_refinement       'CrysAlis RED'
_computing_data_collection       'CrysAlis RED'
_computing_data_reduction        'CrysAlis CCD'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Gemini S Ultra'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10067
_diffrn_reflns_theta_full        62.36
_diffrn_reflns_theta_max         62.36
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    3.247
_exptl_absorpt_correction_T_max  0.8811
_exptl_absorpt_correction_T_min  0.4857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorness
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00044(13)
_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   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0622
_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^)+(0.0594P)^2^+1.6594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                2948
_reflns_number_total             4035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801687v_si_002.cif
_cod_data_source_block           080512-cu
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023824