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Synthesis of Pyrroles by Gold(I)-Catalyzed Amino-Claisen Rearrangement of N-Propargyl Enaminone Derivatives

Akio Saito*, Tomoyo Konishi and Yuji Hanzawa*

*Laboratory of Organic Reaction Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan, Email: akio-saiac.shoyaku.ac.jp, hanzawayac.shoyaku.ac.jp

A. Saito, O. Konishi, Y. Hanzawa, Org. Lett., 2010, 12, 372-374.

DOI: 10.1021/ol902716n (free Supporting Information)


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Abstract

A cationic N-heterocyclic carbene-gold(I) complex catalyzes the formation of tri- and tetrasubstituted pyrroles from N-propargyl β-enaminone derivatives via an amino-Claisen rearrangement to yield α-allenyl β-enaminones and subsequent cyclization of these intermediates.

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proposed reaction pathway



Key Words

Pyrroles, Claisen Rearrangement


ID: J54-Y2010-0210