Stereoselective synthesis of chiral 3,4,5-trisubstituted 1,5-dihydropyrrol-2-ones from azadienes

Authors
Bandini, E Martelli, G Spunta, G Bongini, A Panunzio, M Piersanti, G
Citation
E. Bandini et al., Stereoselective synthesis of chiral 3,4,5-trisubstituted 1,5-dihydropyrrol-2-ones from azadienes, TETRAHEDR-A, 10(8), 1999, pp. 1445-1449
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
8
Year of publication
1999
Pages
1445 - 1449
Database
ISI
SICI code
0957-4166(19990423)10:8<1445:SSOC31>2.0.ZU;2-9
Abstract
A new access to enantiopure 3-phthalimido-4-amino-5-(1-hydroxyalkyl) 1,5-di hydropyrrol-2-ones has been developed from 1,3-azadienes. Stereoselective L ewis acid catalyzed addition of a cyano group to an azadiene, followed by i ntramolecular ring closure, in a four-step one-pot synthesis, results in th e formation of gamma-lactams in satisfactory yields. (C) 1999 Elsevier Scie nce Ltd. All rights reserved.