Ultrasound-Promoted Formation
of Isopentenyl Alcohol Dianion: Straightforward Synthesis
of Perhydrofuro[2,3-b]furans

Francisco Alonso; Mamen Rodríguez-Fernández; Daniel Sánchez; Miguel Yus

doi:10.1055/s-0030-1258168

PAPER

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;

Abstract

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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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Referenzen

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