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", Università di Firenze, Via
della Lastruccia 13, I-50019 Sesto Fiorentino, Italy, Email: ernesto.occhiato
unifi.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
