Synthesis and Properties of a Novel Pyridineoxazoline Containing Optically Active Helical Polymer as a Catalyst Ligand for Asymmetric Diels-Alder Reaction.
Heng Wang, Na Li, Jie Zhang, Xinhua Wan
Index: Chirality 27 , 523-31, (2015)
Full Text: HTML
Abstract
A novel pyridineoxazoline (PyOx) containing helical polymer, poly{(-)-(S)-4-tert-butyl-2-[5-(4-tert-butylphenyl)-3-vinylpyridin-2-yl]-oxazoline} (PA), was designed and synthesized to approach the effect of chain conformation on the catalytic property. Its complex with Cu(OTf)(2) , i.e., Cu(II)-PA, was employed to catalyze the homogeneous Diels-Alder (D-A) reaction of alkenoyl pyridine N-oxides with cyclopentadiene in tetrahydrofuran. Compared with the previously reported copper complex, Cu(II)-P1 (RSC Advances, 2015, 5, 2882), which was derived from a nonhelical poly[(-)-(S)-4-tert-butyl-2-(3-vinylpyridin-2-yl)-oxazoline], Cu(II)-PA exhibited a remarkably enhanced enantioselectivity and reaction rate. However, its enantioselectivity was lower than the Cu(II) complex of (-)-(S)-4-tert-butyl-2-[5-(4-tert-butylphenyl)-3-vinylpyridin-2-yl]-oxazoline (Cu(II)-A), a low molar mass model compound.© 2015 Wiley Periodicals, Inc.
Related Compounds
Related Articles:
2014-08-01
[J. Pharm. Biomed. Anal. 97 , 141-50, (2014)]
Clay catalyzed RNA synthesis under Martian conditions: Application for Mars return samples.
2015-06-26
[Biochem. Biophys. Res. Commun. 462 , 99-104, (2015)]
2015-12-01
[J. Mater. Sci. Mater. Med. 26 , 275, (2015)]
2014-01-01
[BMC Cancer 14 , 841, (2014)]
2014-07-01
[Lipids 49(7) , 665-75, (2014)]