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Letter

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

Supporting Info

Helge Menz and Stefan F. Kirsch*

Department Chemie, Technische Universitt Mnchen, Lichtenbergstrasse 4, 85747 Garching, Germany

Org. Lett., 2006, 8 (21), pp 4795–4797

DOI: 10.1021/ol061856x

Publication Date (Web): September 15, 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.

, stefan.kirsch@ch.tum.de

Abstract

The application of easily accessed propargyl vinyl ethers for the synthesis of monocyclic 2H-pyrans was achieved. Under the reaction conditions, highly substituted heterocycles were obtained in moderate to excellent yields. The one-pot sequence proceeds via a Ag(I)-catalyzed propargyl-Claisen rearrangement, followed by a base-catalyzed isomerization, and 6π-oxaelectrocyclization, leading to the formation of stable 2H-pyrans.

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Published In Issue October 12, 2006
Received July 27, 2006

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Letter

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Gold(I)-Catalyzed Synthesis of Highly Substituted Furans

DABCO-Catalyzed Reaction of α-Halo Carbonyl Compounds with Dimethyl Acetylenedicarboxylate: A Novel Method for the Preparation of Polysubstituted Furans and Highly Functionalized 2H-Pyrans

Efficient Diastereoselective Synthesis of Trifarane-Type Sesquiterpenes, Trifarienols A and B

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