The Lewis acid-catalyzed nazarov reaction of 2-(n-methoxycarbonylamino)-1,4-pentadien-3-ones

Paolo Larini; Antonio Guarna; Ernesto G Occhiato

doi:10.1021/ol053071h

The Lewis acid-catalyzed nazarov reaction of 2-(n-methoxycarbonylamino)-1,4-pentadien-3-ones

Org Lett. 2006 Feb 16;8(4):781-4. doi: 10.1021/ol053071h.

Authors

Paolo Larini¹, Antonio Guarna, Ernesto G Occhiato

Affiliation

¹ Dipartimento di Chimica Organica U. Schiff, Università di Firenze, Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy.

PMID: 16468766
DOI: 10.1021/ol053071h

Abstract

[reaction: see text] A highly efficient carbonylative Suzuki-Miyaura coupling reaction of lactam-derived vinyl triflates and alkenylboronic acids afforded 2-(N-methoxycarbonylamino)-1,4-pentadien-3-ones as suitable substrates for the Nazarov reaction. The most competent Lewis acids for the Nazarov reaction were Cu(OTf)(2) (2 mol %) and Sc(OTf)(3) (3 mol %) in DCE, which provided the Nazarov products in excellent yield. As both the carbonylative coupling and the subsequent Nazarov reaction were high yielding, the overall methodology is a concise and efficient route to [1]pyrindine systems.