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Letter

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

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Paolo Larini, Antonio Guarna, and Ernesto G. Occhiato*

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

Org. Lett., 2006, 8 (4), pp 781–784

DOI: 10.1021/ol053071h

Publication Date (Web): January 27, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ernesto.occhiato@unifi.it

Abstract

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.

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Published In Issue February 16, 2006
Received December 19, 2005

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Letter

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Cyclization of Cross-Conjugated Trienes: The Vinylogous Nazarov Reaction

Catalytic Asymmetric Nazarov Reactions Promoted by Chiral Lewis Acid Complexes

Catalytic, Asymmetric Michael Reactions of Cyclic Diketones with β,γ-Unsaturated α-Ketoesters

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