One-Pot Synthesis of Functionalized β-Fluoroalkylated Mannich-Type Products from N-Aryl N,O-Acetals

Dedicated to Professor Dr. Rolf Huisgen on the occasion of his 95^th birthday

Abstract

A variety of functionalized β-amino-β-fluoroalkyl carbonyl compounds are accessible via a novel one-pot Mannich-type reaction of CF₂- and CF₃-containing N-aryl N,O-acetals with lithium enolates of ketones, esters, and nitriles. The resulting β-fluoroalkylated β-aminocarbonyl compounds are promising peptide surrogates to be used in drug development and for biological applications.

Key words

fluoroalkylated compounds - N,O-acetals - trifluoroethylamine - difluoroethylamine - Mannich-type reaction

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