Synthesis 2014; 46(07): 943-946
DOI: 10.1055/s-0033-1340662
paper
© Georg Thieme Verlag Stuttgart · New York

Transacetalization of Acetals with Butane-1,2,4-triol Using Cobalt(II) Chloride and Chlorotrimethylsilane

Umberto Maria Battisti*
Department of Life Sciences, University of Modena and Reggio Emilia, Via G. Campi 183, 41125 Modena, Italy   Fax: +39(059)2055131   eMail: 38512@studenti.unimore.it
,
Claudia Sorbi
Department of Life Sciences, University of Modena and Reggio Emilia, Via G. Campi 183, 41125 Modena, Italy   Fax: +39(059)2055131   eMail: 38512@studenti.unimore.it
,
Silvia Franchini
Department of Life Sciences, University of Modena and Reggio Emilia, Via G. Campi 183, 41125 Modena, Italy   Fax: +39(059)2055131   eMail: 38512@studenti.unimore.it
,
Annalisa Tait
Department of Life Sciences, University of Modena and Reggio Emilia, Via G. Campi 183, 41125 Modena, Italy   Fax: +39(059)2055131   eMail: 38512@studenti.unimore.it
,
Livio Brasili
Department of Life Sciences, University of Modena and Reggio Emilia, Via G. Campi 183, 41125 Modena, Italy   Fax: +39(059)2055131   eMail: 38512@studenti.unimore.it
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Publikationsverlauf

Received: 15. November 2013

Accepted after revision: 20. Dezember 2013

Publikationsdatum:
21. Januar 2014 (eFirst)

Abstract

Transacetalization of acetals with butane-1,2,4-triol was carried out using cobalt(II) chloride and chlorotrimethylsilane as catalysts. The reaction occurs under mild conditions in acetonitrile and with a short reaction time. The synergic effect of the two Lewis acids catalyzes the conversion of butane-1,2,4-triol into (2-alkyl- or 2-aryl-1,3-dioxan-4-yl)methanol derivatives with high regiospecificity and diasteroselectivity.

 
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