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

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.