Synthesis of bicyclic lactams via ring closing olefin metathesis and intramolecular Heck reaction

Authors
Lennartz, M Steckhan, E
Citation
M. Lennartz et E. Steckhan, Synthesis of bicyclic lactams via ring closing olefin metathesis and intramolecular Heck reaction, SYNLETT, (3), 2000, pp. 319-322
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
3
Year of publication
2000
Pages
319 - 322
Database
ISI
SICI code
0936-5214(200003):3<319:SOBLVR>2.0.ZU;2-B
Abstract
The application of the ring closing olefin metathesis and the intramolecula r Heck reaction as key steps in the synthesis of 6,5-and 7,5-fused enantiom erically pure bicyclic lactams starting from a chiral pyrrolidone is shown. The diolefinic cyclization precursors can be obtained by a combined electr ochemical oxidation- N-acyliminium coupling reaction and a subsequent N-alk ylation using an unsaturated alkyl bromide.