Enantioselectivity Investigation of Short Polar Peptides with Different Positions in the Michael Reaction

Abstract

This work reports the effectiveness of short polar peptides as asymmetric catalysts in Michael reactions to attain good yields of enantio- and diastereoselective isomers. In a comparison, glutamic acid and histidine produced greater ee and yields when they were applied as the second amino acid in short trimeric peptides. These short polar peptides were found to be efficient organocatalysts for the asymmetric Michael addition reaction in water.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

GRAPHICAL ABSTRACT

Keywords:

• Asymmetric
• Michael reaction
• organocatalyst
• short polar peptide

Notes

^a Isolated yield of mixture of syn/anti based on nitrostyrene.

^b Diastereomeric ratio, determined by ¹H NMR.

^c Enantiomeric excess, determined by chiral-phase HPLC analysis.