Stereocontrolled Formation of Ketomethylene Isosteres through Tandem Chain Extension Reactions

Authors

Weimin Lin, University of New HampshireFollow
Nancy Tryder, University of New Hampshire
Fan Su, University of New Hampshire
Charles K. Zercher, University of New HampshireFollow
Jerry P. Jasinski, University of New HampshireFollow
Ray J. Butcher, Howard UniversityFollow

Abstract

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.

Department

Chemistry

Publication Date

10-1-2006

Journal Title

Journal of Organic Chemistry

Publisher

American Chemical Society

Digital Object Identifier (DOI)

10.1021/jo061184o

Document Type

Article

Recommended Citation

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.

Rights

Copyright © 2006, American Chemical Society