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Synthesis of Stable 2H-Pyran-5-carboxylates via a Catalyzed Propargyl-Claisen Rearrangement/Oxa-6π Electrocyclization Strategy

Helge Menz and Stefan F. Kirsch*

*Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany, Email: stefan.kirschch.tum.de

H. Menz, S. F. Kirsch, Org. Lett., 2006, 8, 4795-4797.

DOI: 10.1021/ol061856x (free Supporting Information)


Abstract

A one-pot sequence via a Ag(I)-catalyzed propargyl-Claisen rearrangement of easily accessed propargyl vinyl ethers, followed by a base-catalyzed isomerization, and 6π-oxaelectrocyclization, leads to the formation of stable 2H-pyrans.

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Gold(I)-Catalyzed Synthesis of Highly Substituted Furans

M. H. Suhre, M. Reif, S. F. Kirsch, Org. Lett., 2005, 7, 3873-3876.


Key Words

2H-Pyrans, Claisen rearrangement


ID: J54-Y2006-3240