Stereoselective Synthesis of Highly Substituted Δ1-Pyrrolines: exo-Selective 1,3-Dipolar Cycloaddition Reactions with Azlactones
Satyamaheshwar Peddibhotla; Jetze J. Tepe; Journal of the American Chemical Society 126 (2004) 12776–12777; doi:10.1021/ja046149i

data_4113023
_publ_section_title
;
 Stereoselective Synthesis of Highly Substituted \D1-Pyrrolines:
 exo-Selective 1,3-Dipolar Cycloaddition Reactions with Azlactones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12776
_journal_page_last               12777
_journal_paper_doi               10.1021/ja046149i
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C19 H23 N O6'
_chemical_formula_weight         361.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.121(2)
_cell_angle_beta                 108.284(2)
_cell_angle_gamma                102.713(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5795(12)
_cell_length_b                   9.5772(14)
_cell_length_c                   13.1432(19)
_cell_measurement_temperature    293(2)
_cell_volume                     947.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8076
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.6274
_exptl_absorpt_correction_T_min  0.5314
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             384
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.015(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   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0674P)^2^+0.3998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1276
_reflns_number_gt                2236
_reflns_number_total             2720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja046149irom20040712_113108.cif
_cod_data_source_block           tepe2t
_cod_database_code               4113023