Alpha-amino acids as acid components in the Passerini reaction: Influence of N-protection on the yield and stereoselectivity

Stanislaw Berlozecki, Wiktor Szymanski, Ryszard Ostaszewski*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

28 Citaten (Scopus)

Samenvatting

The Passerini reaction offers an easy access to depsipeptides, when both acid and isocyanide are derived from of.-amino acids. However, racemisation of isocyanides derived from alpha-amino acid esters severely limits their use in the Passerini reaction. In order to overcome this limitation, a study on the influence of the alpha-amino acid N-protecting group on the yield and diastereoisomeric ratio of the product of the Passerini reaction was performed. Six different protecting groups were tested. Their influence turns out to be crucial and is not constant when the amino acid is changed. After optimisation, the Passerini reaction products with cyclohexanone as the carbonyl component were obtained with 99% yield and >98% de. (C) 2008 Elsevier Ltd. All rights reserved.

Originele taal-2English
Pagina's (van-tot)9780-9783
Aantal pagina's4
TijdschriftTetrahedron
Volume64
Nummer van het tijdschrift41
DOI's
StatusPublished - 6-okt-2008

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