Alpha-amino acids as acid components in the Passerini reaction

Autor:	Ryszard Ostaszewski, Stanislaw Berlozecki, Wiktor Szymanski
Přispěvatelé:	Synthetic Organic Chemistry
Jazyk:	angličtina
Rok vydání:	2008
Předmět:	chemistry.chemical_classification Chemistry Isocyanide Organic Chemistry Cyclohexanone AMINOALDEHYDES diastereoselectivity Biochemistry Passerini reaction Amino acid chemistry.chemical_compound isocyanides Yield (chemistry) Drug Discovery Organic chemistry Stereoselectivity INHIBITORS
Zdroj:	Tetrahedron, 64(41), 9780-9783. PERGAMON-ELSEVIER SCIENCE LTD
ISSN:	1464-5416 0040-4020
DOI:	10.1016/j.tet.2008.07.064
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::953e2ebdd68dddbee3fb72a802cca284 https://doi.org/10.1016/j.tet.2008.07.064 Zobrazit plný text záznamu Full Text from ScienceDirect