jo049662n_si_001.pdf (1.09 MB)
Intramolecular Cyclization of Ene-Imine Using Dibutylzirconocene
journal contribution
posted on 2004-09-17, 00:00 authored by Muneyoshi Makabe, Yoshihiro Sato, Miwako MoriThe reaction of ene-imine with Cp2ZrBu2 was carried out. When a crude imine, which was prepared
from ene-aldehyde and primary amine in the presence of MgSO4, was treated with Cp2ZrBu2 at
room temperature overnight, cyclopentane derivative having trans-substituents was obtained in
high yield along with a small amount of cyclopentane derivative having cis-substituents. Presumably, cis-zirconacycle is a thermodynamic product. Reactions using various ene-imines were carried
out. In the case of ene-imine prepared from ene-aldehyde and tBuNH2, only cyclopentane having
cis-substituents was produced. In this reaction, chiral amine was used, and diastereoselective
cyclization of ene-imine was carried out. As a result, cyclopentane derivative having cis-substituents
was obtained in an optically active form after hydrogenolysis of the cyclized compound.