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Anionic Cyclizations of Pentynones and Hexynones: Access to Furan and Pyran Derivatives

✍ Scribed by Thomas Nicola; Ralf Vieser; Wolfgang Eberbach

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 400 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200002)2000:3<527::aid-ejoc527>3.0.co;2-n

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✦ Synopsis

On treatment with base the pentynones 8a؊f undergo anionic addition reactions of the resulting enolate species to the alkyne moiety and afford the 2,5-disubstituted furans 10a؊f in yields ranging from 10Ϫ91%. The proposed mechanism involves the 2-methylene-dihydrofurans 11 as intermediates which tautomerize to yield the observed products. In the case of the α-picolyl derivative 8g both possible enolates 12 and 13 are formed which are subsequently transformed to the products 10g and 14g, respectively. Starting with the

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