Synthesis of fluorescent enone derived alpha-amino acids
Lindsay S Fowler1, David Ellis, Andrew Sutherland
1WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UK G12 8QQ.
Abstract:
The development of a facile and general method for the preparation of enone derived alpha-amino acids is described. The key step involves a Horner-Wadsworth-Emmons reaction between an aspartic acid derived beta-keto phosphonate ester and a range of aldehydes resulting in the formation of highly functionalised alpha-amino acids in good yields. An efficient two-stage deprotection process using mild conditions was developed to give the parent alpha-amino acids. Application of this methodology has produced a novel fluorescent alpha-amino acid that has potential as a biological marker.
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Types of Enols and Enolates
Nitrosation of Enols


