Synthesis of stable 2H-pyran-5-carboxylates via a catalyzed propargyl-Claisen rearrangement/oxa-6pi electrocyclization strategy

[reaction: see text] 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 pro...

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Bibliographic Details
Published in:Organic letters 2006-10, Vol.8 (21), p.4795-4797
Main Authors: Menz, Helge, Kirsch, Stefan F
Format: Article
Language:English
Online Access:Get full text
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Summary:[reaction: see text] 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 6pi-oxaelectrocyclization, leading to the formation of stable 2H-pyrans.
ISSN:1523-7060
1523-7052