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Synlett 2004(10): 1826-1828
DOI: 10.1055/s-2004-829553
DOI: 10.1055/s-2004-829553
LETTER
© Georg Thieme Verlag Stuttgart · New York
Ethyl Propiolate: A Simple and Convenient Peptide Coupling Reagent
Weitere Informationen
Received
26 May 2004
Publikationsdatum:
15. Juli 2004 (online)
Publikationsverlauf
Publikationsdatum:
15. Juli 2004 (online)
Abstract
Ethyl propiolate has been used to activate N-protected amino acids to form a moderately activated vinyl-ester which aminolysis requires a catalytic amount of sodium bisulfite.
Key words
peptide - coupling reagent - sodium bisulfite
- 1
Nájera C. Synlett 2002, 1388 -
2a
Sheehan JC.Cruickshank PA.Boshart GL. J. Org. Chem. 1961, 26: 2525 -
2b
Sheehan JC.Preston J.Cruickshank PA. J. Am. Chem. Soc. 1965, 87: 2492 -
2c
Williams A.Ibrahim IT. J. Am. Chem. Soc. 1981, 103: 7090 - 3
Coste J.Le-Nguyen D.Castro B. Tetrahedron Lett. 1990, 31: 205 - 4
Coste J.Frérot E.Castro B. J. Org. Chem. 1994, 59: 2437 -
5a
Carpino LA. J. Am. Chem. Soc. 1993, 115: 4397 -
5b
Carpino LA.El-Faham A.Minor CA.Albericio F. J. Chem. Soc., Chem. Commun. 1994, 201 -
6a
Chen S.Xu J. Tetrahedron Lett. 1991, 32: 6711 -
6b
Dudash J.Jiang J.Mayer SC.Joullié MM. Synth. Commun. 1993, 23: 349 - Reviews:
-
7a
Albericio F.Chinchilla R.Dodsworth DJ.Nájera C. Org. Prep. Proc. Int. 2001, 33: 203 -
7b
Methods in Organic Chemistry (Houben-Weyl)
Vol. E22a:
Goodman M. Georg Thieme Verlag; Stuttgart: 2002. -
8a
Trost BM. Science 1991, 254: 1471 -
8b
Trost BM. Acc. Chem. Res. 2002, 35: 1471 -
9a
Gais HJ. Angew. Chem., Int. Ed. Engl. 1978, 17: 597 -
9b
Neuenschwander M.Fahmi H.-P.Lienhard U. Helv. Chim. Acta 1978, 61: 2437 -
10a
Ruppin C.Dixneuf P.Lecolier S. Tetrahedron Lett. 1988, 29: 5365 -
10b
Kabouche Z.Bruneau C.Dixneuf P. Tetrahedron Lett. 1991, 32: 5359 - 11
Sato M.Yoneda N.Katagiri N.Watanabe H.Kaneko C. Synthesis 1986, 672 - 12 For a review on the activation of conjugated alkynes with phosphines, see:
Lu X.Zhang C.Xu Z. Acc. Chem. Res. 2001, 34: 535 ; and references cited therein - 15
Van der Auwera C.Vandamme S.Anteunis MJO. Int. J. Pept. Protein Res. 1987, 29: 464
References
The mechanism is believed to imply the catalysis of the tertiary amine (Scheme [1] ) and not a direct Michael addition of the carboxylate since no reaction is observed in the presence of various inorganic bases.
14One referee has suggested that lower yields could be explained by the formation of a Schiff base from by product 13 and the amino ester. However, this kind of by-product was never observed either by TLC or by 1H NMR on the crude mixture.