Stereoselective synthesis of 3-(omega-hydroxyalkyl)-2-pyrrolidinones from alpha-alkylidenelactones and nitromethane

Authors
Otto, A Abegaz, B Ziemer, B Liebscher, J
Citation
A. Otto et al., Stereoselective synthesis of 3-(omega-hydroxyalkyl)-2-pyrrolidinones from alpha-alkylidenelactones and nitromethane, TETRAHEDR-A, 10(17), 1999, pp. 3381-3389
Citations number
10
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
17
Year of publication
1999
Pages
3381 - 3389
Database
ISI
SICI code
0957-4166(19990827)10:17<3381:SSO3FA>2.0.ZU;2-H
Abstract
Enantiopure 3-(omega-hydroxyalkyl)-2-pyrrolidinones 7 and 9 were synthesise d by Michael-addition of nitromethane to chiral alpha-alkylidenelactones 1 followed by reduction of the resulting 3-(beta-nitroalkyl)-lactones and rin g transformation of the intermediate 3-(beta-aminoalkyl)-lactones. In an an alogous manner the naturally occurring costuslactone 10 was transformed int o the butyrolactam 12. (C) 1999 Elsevier Science Ltd. All rights reserved.