Synthesis of cyclic dipeptides by ring-closing metathesis

Authors
Reichwein, JF Liskamp, RMJ
Citation
Jf. Reichwein et Rmj. Liskamp, Synthesis of cyclic dipeptides by ring-closing metathesis, EUR J ORG C, (12), 2000, pp. 2335-2344
Citations number
40
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
12
Year of publication
2000
Pages
2335 - 2344
Database
ISI
SICI code
1434-193X(200006):12<2335:SOCDBR>2.0.ZU;2-L
Abstract
Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by "amide-t o-amide" cyclization of 2a-g and 8a-c, respectively, by means of ring-closi ng metathesis employing the Grubbs ruthenium catalyst. The influence of add itives as well as the length of the amide substituent were studied. Best yi elds were obtained by cyclization in solution with either lithium fluoroace tate or alpha,alpha-dichlorotoluene as an additive.