Stereocontrolled Formation of Ketomethylene Isosteres through Tandem Chain Extension Reactions
A zinc-mediated chain extension reaction is the key step in the preparation of γ-keto amides derived from amino acids. The use of tandem reaction sequences, in which the intermediate zinc enolate is trapped with electrophilic reagents, results in the incorporation of α-substituents, which mimic the side chains found in natural amino acid systems. Use of the chiral amino acid l-proline as a stereo-directing element provides a diastereoselective route to various ketomethylene isosteres.
Journal of Organic Chemistry
American Chemical Society
Digital Object Identifier (DOI)
Stereocontrolled Formation of Ketomethylene Isosteres through Tandem Chain Extension Reactions, Lin, W.; Tryder, N.; Su, F.; Zercher, C. K., Jasinski, J. P., Butcher, R. J. J. Org. Chem. 2006, 71, 8140-8145.
Copyright © 2006, American Chemical Society