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Synthesis 2010(17): 3013-3020
DOI: 10.1055/s-0030-1258168
DOI: 10.1055/s-0030-1258168
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Ultrasound-Promoted Formation of Isopentenyl Alcohol Dianion: Straightforward Synthesis of Perhydrofuro[2,3-b]furans
Further Information
Received
4 May 2010
Publication Date:
12 July 2010 (online)
Publication History
Publication Date:
12 July 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201017/lookinside/thumbnails/10.1055-s-0030-1258168-1.jpg)
Abstract
Ultrasound has been found to accelerate the formation of isopentenyl alcohol dianion by metalation with butyllithium in diethyl ether-tetrahydrofuran. The reaction of this dianion with carbonyl compounds followed by intramolecular acetalization under Wacker-type conditions provides a direct route for the synthesis of 2-substituted perhydrofuro[2,3-b]furans.
Key words
metalation - ultrasound - polyanions - Wacker-type reaction - cyclization - perhydrofuro[2,3-b]furans
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