A new straightforward synthesis of 2,3-aziridino-gamma-lactones

Authors
de Saint-Fuscien, C Tarrade, A Dauban, P Dodd, RH
Citation
C. De Saint-fuscien et al., A new straightforward synthesis of 2,3-aziridino-gamma-lactones, TETRAHEDR L, 41(33), 2000, pp. 6393-6397
Citations number
71
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
33
Year of publication
2000
Pages
6393 - 6397
Database
ISI
SICI code
0040-4039(20000812)41:33<6393:ANSSO2>2.0.ZU;2-W
Abstract
A concise synthesis of 2,3-aziridino-gamma-lactones starting from commercia lly available alpha,beta-dihydroxy-gamma-lactones is described. The strateg y involves a Michael-type addition of benzylamine onto a key 2-(5H)-furanon -3-yl trifluoromethanesulfonate, followed by in situ cyclization to the azi ridine without lactone-ring-opening. (C) 2000 Elsevier Science Ltd. All rig hts reserved.