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Solid-Phase Synthesis of Dihydropyrans by Heterocycloaddition of a Supported Vinyl Ether: Progress in Functional Diversity

✍ Scribed by Amélie Arboré; Gilles Dujardin; Christian Maignan

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 124 KB
Volume: 2003
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200300417

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✦ Synopsis

Abstract

The carboxypolystyrene‐bound vinyl ether of 1,4‐butanediol smoothly underwent an efficient endo‐selective hetero‐Diels−Alder reaction, under Lewis‐acid conditions, with heterodienes bearing methyl ester, trifluoromethyl and para‐tolylsulfinylmethyl groups at the C‐2 position. Reductive cleavage of the supported adducts afforded functionalized dihydropyrans, which are of particular interest for diversity‐oriented parallel synthesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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