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

Swetlana Wunder; Amrei Deutsch; Carl Deutsch; Anja Hoffmann-Röder

doi:10.1055/s-0035-1561324

Synthesis, Table of Contents

Synthesis 2016; 48(08): 1167-1176
DOI: 10.1055/s-0035-1561324

paper

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

Swetlana Wunder

^aCenter for Integrated Protein Science Munich (CIPSM) at the Department of Chemistry, Ludwig-Maximilians-Universität, Butenandtstr. 5–13, 81377 Munich, Germany Email: anja.hoffmann-roeder@cup.lmu.de

,

Amrei Deutsch

^aCenter for Integrated Protein Science Munich (CIPSM) at the Department of Chemistry, Ludwig-Maximilians-Universität, Butenandtstr. 5–13, 81377 Munich, Germany Email: anja.hoffmann-roeder@cup.lmu.de

,

Carl Deutsch*

^bMedicinal Chemistry, Merck, Frankfurter Str. 250, 64293 Darmstadt, Germany

,

Anja Hoffmann-Röder*

^aCenter for Integrated Protein Science Munich (CIPSM) at the Department of Chemistry, Ludwig-Maximilians-Universität, Butenandtstr. 5–13, 81377 Munich, Germany Email: anja.hoffmann-roeder@cup.lmu.de

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Abstract

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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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References

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