Stereoselective synthesis of a new enantiopure tricyclic beta-lactam derivative via a tricarbonyl(eta(6)-arene)chromium(0) complex

Authors
Del Buttero, P Baldoli, C Molteni, G Pilati, T
Citation
P. Del Buttero et al., Stereoselective synthesis of a new enantiopure tricyclic beta-lactam derivative via a tricarbonyl(eta(6)-arene)chromium(0) complex, TETRAHEDR-A, 11(9), 2000, pp. 1927-1941
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
9
Year of publication
2000
Pages
1927 - 1941
Database
ISI
SICI code
0957-4166(20000519)11:9<1927:SSOANE>2.0.ZU;2-O
Abstract
The tricyclic beta-lactam 5 has been synthesized both in racemic and enanti opure form starting from the enantiomerically pure tricarbonylchromium(0) c omplex 1. The synthetic sequence involves the stereoselective [2+2] cycload dition of 1 with acetoxyacetylketene, followed by intramolecular aromatic n ucleophilic substitution of the fluorine atom. Mechanistic pathways leading to 5 are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.