Asymmetric synthesis of 5-isopropyl-oxazoline-4-imide as syn-hydroxyleucine precursor

Authors
Cardillo, G Gentilucci, L Gianotti, M Tolomelli, A
Citation
G. Cardillo et al., Asymmetric synthesis of 5-isopropyl-oxazoline-4-imide as syn-hydroxyleucine precursor, TETRAHEDR-A, 12(4), 2001, pp. 563-569
Citations number
33
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
4
Year of publication
2001
Pages
563 - 569
Database
ISI
SICI code
0957-4166(20010319)12:4<563:ASO5AS>2.0.ZU;2-4
Abstract
The synthesis of syn N-acetyl-hydroxyleucine methyl ester is reported throu gh the ring expansion of aziridine-2-imides to oxazoline-4-imides. The key steps of the synthesis are the I,il-addition of O-benzylhydroxylamine to un saturated imides, promoted by Lewis acids, and the regio- and stereoselecti ve ring expansion of ti ans-aziridines to trans-oxazolines. (C) 2001 Elsevi er Science Ltd. All rights reserved.