Rapid entry to enantiopure polycyclic beta-lactams via intramolecular nitrone-alkene cycloaddition of 2-azetidinone-tethered alkenylaldehydes

Authors
Alcaide, B Alonso, JM Aly, MF Saez, E Martinez-Alcazar, MP Hernandez-Cano, F
Citation
B. Alcaide et al., Rapid entry to enantiopure polycyclic beta-lactams via intramolecular nitrone-alkene cycloaddition of 2-azetidinone-tethered alkenylaldehydes, TETRAHEDR L, 40(29), 1999, pp. 5391-5394
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
29
Year of publication
1999
Pages
5391 - 5394
Database
ISI
SICI code
0040-4039(19990716)40:29<5391:RETEPB>2.0.ZU;2-A
Abstract
New enantiomerically pure fused 2 or bridged 3 polycyclic beta-lactam syste ms are regio- and stereoselectively prepared via intramolecular nitrene-alk ene cycloaddition of 2-azetidinone-tethered alkenyl-aldehydes 1. The regios electivity of the cycloaddition can be tuned by moving the alkene substitue nt from N1 to C3 on the 2-azetidinone ring. (C) 1999 Elsevier Science Ltd. All rights reserved.