Enol esters: versatile substrates for Mannich-type...[Org Lett. 2007]

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1: Org Lett. 2007 Oct 11;9(21):4199-202. Epub 2007 Sep 15. Links

Enol esters: versatile substrates for Mannich-type multicomponent reactions.

Isambert N, Cruz M, Arévalo MJ, Gómez E, Lavilla R.

Institute for Research in Biomedicine, Barcelona Science Park, Josep Samitier 1-5, 08028 Barcelona, Spain.

The interaction of cyclic enol esters with diversely substituted anilines and ethyl glyoxalate yields, under Sc(OTf)3 catalysis, disubstituted N-aryl lactams in a multicomponent reaction. The protocol allows access to the trans stereoisomers after an epimerization of the initial mixture in which the cis isomers predominate. Vinyl acetate yields quinoline derivatives, whereas isopropenyl acetate leads to the corresponding Mannich adducts.

PMID: 17867693 [PubMed - indexed for MEDLINE]

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