Aza- 3,3 -claisen enolate rearrangement in vinylaziridines: Stereoselective synthesis of mono-, di-, and trisubstituted seven-membered lactams
2001 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 7, no 1, 94-98 p.Article in journal (Refereed) Published
Several 2,3-disubstituted vinylaziridines have been N-acylated and subjected to LiHMDS in THF at - 78 degreesC. Upon warming to room temperature, the resulting amide enolates underwent a highly stereoselective [3,3]-sigmatropic rearrangement to give mono-, di-, and trisubstituted seven-membered lactams in good yields. The scope and limitations of the process have been investigated by using variously substituted vinylaziridines. A kinetically controlled process proceeding through a six-membered boatlike transition state assembly has been invoked to explain the stereochemical outcome of the reaction.
Place, publisher, year, edition, pages
2001. Vol. 7, no 1, 94-98 p.
C-C coupling, lactams, rearrangements, vinylaziridines, aza-wittig rearrangement, aza-<2,3>-wittig rearrangements, pyrrolizidine alkaloids, organocopper reagents, claisen rearrangement, entry, selectivity, annulation, aminolysis, isosteres
IdentifiersURN: urn:nbn:se:kth:diva-20288ISI: 000166419500009OAI: oai:DiVA.org:kth-20288DiVA: diva2:338982
QC 201005252010-08-102010-08-10Bibliographically approved