The Hydrogenation of (4R)-4-[(tert-Butoxycarbonyl)amino]-2-methyl-2-penten-5-olide: A Precursor of trans-4-Methylproline

Autor:	Marta Nevalainen, Ari M. P. Koskinen
Rok vydání:	2001
Předmět:	chemistry.chemical_classification Solvent system chemistry.chemical_compound 4-methylproline Chemistry Organic Chemistry Organic chemistry Recrystallization (metallurgy) chemistry.chemical_element Diethyl ether Catalysis Amino acid Rhodium
Zdroj:	Synlett. 2001:0640-0642
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-2001-13380
Popis:	(4R)-4[(tert-Butoxycarbonyl)amino]-2-methyl-2-penten-5-olide was synthesized and hydrogenated under various catalyst/solvent systems. The best cis/trans ratio was obtained with Rh/C in diethyl ether (dr = 90 : 10). After one recrystallization, (2S,4R)-4-[(tert-butoxycarbonyl)amino]-2-methylpentan-5-olide was obtained (dr = 95 : 5, ee = 97%), which is a precursor of trans-4-methylproline.
Databáze:	OpenAIRE
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