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Paper | Special issue | Vol 59, No. 1, 2003, pp.189-198
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S17
Hexafluoroacetone as Protection and Activation Reagent in Amino Acid and Peptide Chemistry Regiospecific α-Functionalization of Aspartic Acid

Klaus Burger,* Torsten Lange, and Martin Rudolph

*Department of Organic Chemistry, University of Leipzig, Johannisallee 29, D-04103 Leipzig, Germany

Abstract

A highly efficient method for regiospecific α-functionalization of aspartic acid is described. Key step is the synthesis of a N-protected and regioselectively α-carboxy-activated heterocyclic intermediate from aspartic acid and hexafluoroacetone. The new strategy offers i.a. a two step access to the sweetener Aspartame® and to libraries of aspartame analogues.