An N-heterocyclic carbene-catalyzed [8 + 3] annulation of tropone and enals via homoenolate.
Vijay Nair, Manojkumar Poonoth, Sreekumar Vellalath, Eringathodi Suresh, Rajasekaran Thirumalai
Index: J. Org. Chem. 71(23) , 8964-5, (2006)
Full Text: HTML
Abstract
A novel protocol for the annulation of tropone to enals involving nucleophilic heterocyclic carbene (NHC) catalyzed homoenolate formation has been developed. Interestingly, the reaction led to bicyclic delta-lactones instead of the expected gamma-spirolactones, presumably by the uncommon [8 + 3] annulation pathway. The strategy works well with a variety of enals.
Related Compounds
Related Articles:
Benzo[cd]azulene skeleton: azulene, heptafulvene, and tropone derivatives.
2009-12-03
[Org. Lett. 11(23) , 5363-5, (2009)]
Tropylium tetrafluoroborate, a novel substrate for aldehyde oxidase.
1986-10-30
[Biochem. Biophys. Res. Commun. 140(2) , 609-15, (1986)]
2015-06-01
[Z. Naturforsch., C, J. Biosci. 59(3-4) , 184-6, (2004)]
Pernambucone, a new tropone derivative from Croton argyroglossum.
2009-05-01
[Pharmazie 64(5) , 350-1, (2009)]
2014-02-12
[J. Am. Chem. Soc. 136(6) , 2625-9, (2014)]