The Journal of organic chemistry

Morpholine-Based Immonium and Halogenoamidinium Salts as Coupling Reagents in Peptide Synthesis1

A El-Faham, F Albericio

Index: El-Faham, Ayman; Albericio, Fernando Journal of Organic Chemistry, 2008 , vol. 73, # 7 p. 2731 - 2737

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Citation Number: 58

Abstract

Here we describe a new family of N-form immonium-type coupling reagents that differ in their carbocation skeleton structure. The N-methylpiperazine derivative failed to form immonium salts, while the thiomorpholine derivative did not give better results than the coupling reagents currently used. The presence of the morpholine had a marked influence on the solubility and stability as well as the reactivity of the reagent. Finally, the ...