A new synthesis of exo-methylene butyrolactones from nitroalkanes

Authors
Ballini, R Bosica, G Livi, D
Citation
R. Ballini et al., A new synthesis of exo-methylene butyrolactones from nitroalkanes, SYNTHESIS-S, (10), 2001, pp. 1519-1522
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
10
Year of publication
2001
Pages
1519 - 1522
Database
ISI
SICI code
0039-7881(200108):10<1519:ANSOEB>2.0.ZU;2-#
Abstract
A versatile route to exo-methylene butyrolactones was developed by employin g a three step reaction sequence consisting of Michael addition of primary nitroalkanes I to ethyl (2-bromomethyl)acrylate (2), then Nef conversion of the nitro derivatives 3, and subsequent lactonization of the obtained keto esters 4. The method is chemoselective for important functionalities such as ester, C=C double bond and hydroxyl.