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The Lewis Acid-Catalyzed Nazarov Reaction of 2-(N-Methoxycarbonylamino)-1,4-pentadien-3-ones

Paolo Larini, Antonio Guarna and Ernesto G. Occhiato*

*Dipartimento di Chimica Organica "U. Schiff", UniversitÓ di Firenze, Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy, Email: ernesto.occhiatounifi.it

P. Larini, A. Guarna, E. G. Occhiato, Org. Lett., 2006, 8, 781-784.

DOI: 10.1021/ol053071h (free Supporting Information)


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Abstract

A carbonylative Suzuki-Miyaura coupling reaction of lactam-derived vinyl triflates and alkenylboronic acids afforded 2-(N-methoxycarbonylamino)-1,4-pentadien-3-ones in good yield. The most efficient Lewis acids for a subsequent Nazarov reaction were Cu(OTf)2 and Sc(OTf)3 in DCE, which provided the Nazarov products in excellent yield.  The overall methodology is a concise and efficient route to [1]pyrindine systems.

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Key Words

Enones, Nazarov Cyclization, Suzuki Coupling


ID: J54-Y2006-330