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Solid‐Phase Synthesis of Dihydropyrans by Heterocycloaddition of a Supported Vinyl Ether: Progress in Functional Diversity
Author(s) -
Arboré Amélie,
Dujardin Gilles,
Maignan Christian
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300417
Subject(s) - chemistry , lewis acids and bases , adduct , trifluoromethyl , ether , vinyl ether , cleavage (geology) , organic chemistry , stereochemistry , medicinal chemistry , polymer chemistry , catalysis , alkyl , polymer , geotechnical engineering , fracture (geology) , engineering , copolymer
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)