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Org Lett. 2006 Feb 16;8(4):781-4.

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

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

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.

PMID:
16468766
DOI:
10.1021/ol053071h
[PubMed]
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