Synthesis 2016; 48(08): 1167-1176
DOI: 10.1055/s-0035-1561324
paper
© Georg Thieme Verlag Stuttgart · New York

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

Swetlana Wunder
Center 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
Center 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*
Medicinal Chemistry, Merck, Frankfurter Str. 250, 64293 Darmstadt, Germany
,
Anja Hoffmann-Röder*
Center 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
› Author Affiliations
Further Information

Publication History

Received: 05 November 2015

Accepted after revision: 15 December 2015

Publication Date:
26 January 2016 (eFirst)

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

Supporting Information

 
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