The hydrogenation of (4R)-4-[(tert-butoxycarbonyl)amino]-2-methyl-2-penten-5-olide: A precursor of trans-4-methylproline

Authors
Nevalainen, M Koskinen, AMP
Citation
M. Nevalainen et Amp. Koskinen, The hydrogenation of (4R)-4-[(tert-butoxycarbonyl)amino]-2-methyl-2-penten-5-olide: A precursor of trans-4-methylproline, SYNLETT, (5), 2001, pp. 640-642
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
5
Year of publication
2001
Pages
640 - 642
Database
ISI
SICI code
0936-5214(200105):5<640:THO(>2.0.ZU;2-Y
Abstract
(4R)-4-[(tert-Butoxycarbonyl)amino]-2-methyl-2-penten-5-olide was synthesiz ed and hydrogenated under various catalyst/solvent systems. The best cis/tr ans ratio was obtained with Rh/C in diethyl ether (dr = 90:10). After one r ecrystallization, (2S,4R)4-[(tert-butoxycarbonyl)amino]-2-methylpentan-5-ol ide was obtained (dr = 95:5, ee = 97%), which is a precursor of trans-4-met hylproline.