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Synthesis 2009(18): 3136-3142  
DOI: 10.1055/s-0029-1217602
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized l-Cysteine and l-Methionine by Reaction with Electron-Deficient Acetylenes

Boris A. Trofimov*, Anastasiya G. Mal’kina, Olesya A. Shemyakina, Valentina V. Nosyreva, Angela P. Borisova, Spartak S. Khutsishvili, Leonid B. Krivdin
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
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Publikationsverlauf

Received 28 April 2009
Publikationsdatum:
10. Juli 2009 (online)

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Abstract

A novel families of nonconventionally functionalized amino acids have been synthesized in almost quantitative yields by chemo-, regio- and stereospecific addition of l-cysteine and l-­methionine to electron-deficient functionalized acetylenes (cyano-acetylenes and methyl 4-hydroxy-4-methylpent-2-ynoate) under mild conditions (water, r.t., 2-5 h). Thus, for the first time, the uncommonly functionalized optically active amino acids composing of l-cysteine and l-methionine structural units along with cinnamic acid, dihydrofuranone, iminodihydrofuran, and other biologically important functionalities are readily available.

Key words

alkynes - amino acids - nucleophilic addition - cyclization

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