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Synthesis 2010(17): 3013-3020  
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

Francisco Alonso*, Mamen Rodríguez-Fernández, Daniel Sánchez, Miguel Yus*
Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
Fax: +34(965)903549; e-Mail: falonso@ua.es; e-Mail: yus@ua.es;
Further Information

Publication History

Received 4 May 2010
Publication Date:
12 July 2010 (online)

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Corrected by:

Ultrasound-Promoted Formation of Isopentenyl Alcohol Dianion: Straightforward Synthesis of Perhydrofuro[2,3-b]furansSynthesis 2011; 2011(11): 1814-1814
DOI: 10.1055/s-0030-1260042

Corrected by:

RuO4-Catalyzed Oxidation Reactions of N-Alkylisoxazolino-2-azanorbornane Derivatives: An Expeditious Route to Tricyclic γ-LactamsSynthesis 2011; 2011(13): e2-e2
DOI: 10.1055/s-0030-1260072

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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